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Angell CA, Ansari Y, Zhao Z (2012) Ionic liquids: past, present and future. Faraday Discuss 154:9–27
de Mejere A, Diederich F (eds) (2004) Metal-catalysed cross-coupling reactions. Wiley, Weinheim, and references therein
Nicolaou KC, Bulger PG, Sarlah D (2005) Palladium-catalyzed cross-coupling reactions in total synthesis. Angew Chem Int Ed 44:4442–4449
Negishi E (2007) Transition metal-catalyzed organometallic reactions that have revolutionized organic synthesis. Bull Chem Soc Jpn 80:233–257
Corbet JP, Mignani G (2006) Selected patented cross-coupling reaction technologies. Chem Rev 106:2651–2710, and references therein
Deeth RJ, Smith A, Hii KK, Brown JM (1998) The Heck olefination reaction a DFT study of the elimination pathway. Tetrahedron Lett 39:3229–3232
Ludwig JM, Strömberg S, Svensson M, Åkermark B (1999) An exploratory study of regiocontrol in the Heck type reaction influence of solvent polarity and bisphosphine ligands. Organometallics 18:970–975
Amatore C, Jutand A (1999) Mechanistic and kinetic studies of palladium catalytic systems. J Organomet Chem 576:254–278
von Schenck H, Åkermark B, Svensson M (2003) Electronic control of the regiochemistry in the Heck reaction. J Am Chem Soc 125:3503–3508
Hills ID, Fu GC (2004) Elucidating reactivity differences in palladium-catalyzed coupling processes: the chemistry of palladium hydrides. J Am Chem Soc 126:13178–13179
Fristrup P, Le Quement S, Tanner D, Norrby PO (2004) Reactivity and regioselectivity in the Heck reaction: Hammett study of 4-substituted styrenes. Organometallics 23:6160–6165
Singh R, Sharma M, Mamgain R, Rawat DS (2008) Ionic liquids: a versatile medium for palladium-catalyzed reactions. J Braz Chem Soc 19:357–379
Trzeciak AM, Ziòlkowski JJ (2007) The role of ionic liquids in palladium-catalyzed C–C bond-forming reactions. In: Yamamoto K (ed) Advances organometallic chemistry research. Nova Science Publishers, New York
Bellina F, Chiappe C (2010) The Heck reaction in ionic liquids: progress and challenges. Molecules 15:2211–2245
Prechtl MHG, Scholten JD, Dupont J (2010) Carbon-carbon cross coupling reactions in ionic liquids catalysed by palladium metal nanoparticles. Molecules 15:3441–3461
Olivier-Bourbigou H, Magna L, Morvan D (2010) Ionic liquids and catalysis: recent progress from knowledge to applications. Appl Cat A: Gen 373:1–56
Hallett JP, Welton T (2011) Room-temperature ionic liquids: solvents for synthesis and catalysis 2. Chem Rev 111:3508–3576
Heck RF (1991) TITOLO? In: Trost BM, Fleming I (eds) Comprehensive organic synthesis, vol 4. Pergamon, Oxford
Herrmann WA (1996) TITOLO? In: Cornils B, Herrmann WA (eds) Applied homogeneous catalysis with organometallic compounds. VCH, Weinheim
de Meijere A, Meyer FE (1994) TITOLO? Angew Chem Int Ed Engl 33:2379–2411
Cabri W, Candiani I (1995) Recent developments and new perspectives in the Heck reaction. Acc Chem Res 28:2–7
Crisp GT (1998) Variations on a theme – recent developments on the mechanism of the Heck reaction and their implications for synthesis. Chem Soc Rev 27:427–436
Genet JP, Savignac MJ (1999) Recent developments of palladium(0) catalyzed reactions in aqueous medium. J Organomet Chem 576:305–317
Whitcombe NJ, Hii KK, Gibson SE (2001) Advances in the Heck chemistry of aryl bromides and chlorides. Tetrahedron 57:7449–7476
Herrmann WA, Öfele K, Preysing D, Schneider SK (2003) Phospha-palladacycles and N-heterocyclic carbene palladium complexes: efficient catalysts for CC-coupling reactions. J Organomet Chem 687:229–248
Blaser H-U, Indolese A, Naud F, Nettekoven U, Schnyder A (2004) Industrial R&D on catalytic CC and CN coupling reactions: a personal account on goals, approaches and results. Adv Synth Catal 346:1583–1598
Christmann U, Vilar R (2005) Monoligated palladium species as catalysts in cross-coupling reactions. Angew Chem Int Ed 44:366–374
Dominguez B, Iglesia B, de Lera AR (1998) Tetraenylstannanes in the synthesis of retinoic acid and its ring-modified analogues. J Org Chem 63:4135–4139
Lipshutz BH, Ullman B, Lindsley C, Pecchi S, Buzard DJ, Dickson D (1998) A new bromo trienyne: synthesis of all-E, conjugated tetra-, penta-, and hexaenes common to oxo polyene macrolide antibiotics. J Org Chem 63:6092–6093
Pinto A, Jia Y, Neuville L, Zhu J (2007) Palladium-catalyzed enantioselective domino Heck–cyanation sequence: development and application to the total synthesis of esermethole and physostigmine. Chem Eur J 13:961–967
Mizoroki T, Mori K, Ozaki A (1971) Arylation of olefin with aryl iodide catalyzed by palladium. Bull Chem Soc Jpn 44:581–581
Heck RF, Nolley JP Jr (1972) Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J Org Chem 37:2320–2322
Dounay AB, Overman LE (2003) The asymmetric intramolecular Heck reaction in natural product total synthesis. Chem Rev 103:2945–2963
Beletskaya IP, Cheprakov AV (2000) The Heck reaction as a sharpening stone of palladium catalysis. Chem Rev 100:3009–3066
Balanta A, Godard C, Claver C (2011) Pd nanoparticles for C–C coupling reactions. Chem Soc Rev 40:4973–4985
Grasa GA, Viciu MS, Huang J, Nolan SP (2001) Amination reactions of aryl halides with nitrogen-containing reagents mediated by palladium/imidazolium salt systems. J Org Chem 66:7729–7737
Gstöttma CWK, Böhm VPW, Herdtweck E, Grosche M, Herrmann WA (2002) A defined N-heterocyclic carbene complex for the palladium-catalyzed suzuki cross-coupling of aryl chlorides at ambient temperatures. Angew Chem Int Ed 41:1363–1365
Yin J, Rainka MP, Zhang X-X, Buchwald SL (2002) A highly active Suzuki catalyst for the synthesis of sterically hindered biaryls: novel ligand coordination. J Am Chem Soc 124:1162–1163
Beare NA, Hartwig JF (2002) Palladium-catalyzed arylation of malonates and cyanoesters using sterically hindered trialkyl- and ferrocenyldialkylphosphine ligands. J Org Chem 67:541–555
Selvakumar K, Zapf A, Beller M (2002) New palladium carbene catalysts for the Heck reaction of aryl chlorides in ionic liquids. Org Lett 4:3031–3033
Rohlich C, Kohler K (2010) Tetraalkylammonium-free Heck olefination of deactivated chloroarenes by using a macrocyclic catalyst precursor. Chem Eur J 16:2363–2365
Xu HJ, Zhao YQ, Zhou XF (2011) Palladium-catalyzed Heck reaction of aryl chlorides under mild conditions promoted by organic ionic bases. J Org Chem 76:8036–8041k
Bader RR, Baumeister P, Blaser HU (1996) Catalysis at Ciba-Geigy. Chimia 50:99–105
Jeffery T (1984) Palladium-catalysed vinylation of organic halides under solid–liquid phase transfer conditions. J Chem Soc Chem Commun 1287–1289
Jeffery T (1985) Highly stereospecific palladium-catalysed vinylation of vinylic halides under solid–liquid phase transfer conditions. Tetrahedron Lett 26:2667–2669
Jeffery T (1996) On the efficiency of the tetralkylammonium salts in the Heck type reactions. Tetrahedron 52:10113–10130
Beller M, Fischer H, Kühlein K, Reisinger C-P, Herrmann WA (1996) First palladium-catalyzed Heck reactions with efficient colloidal catalyst systems. J Organomet Chem 520:257–259
Reetz MT, Lohmer G, Schwickardi R (1998) A New catalyst system for the Heck reaction of unreactive aryl halides. Angew Chem Int Ed Engl 37:481–483
Herrmann WA, Elison M, Fisher J, Köcher C, Artus GRJ (1995) Metal complexes of N-heterocyclic carbenes as new structural principle for catalysts in homogeneous catalysis. Angew Chem Int Ed Engl 14:2371–2374
Kaufmann D, Nouroozian M, Henze H (1996) Molten salts as an efficient medium for palladium catalyzed C-C coupling reactions. Synlett 1091–1092
Herrmann WA, Böhm VPW (1999) Heck reaction catalyzed by phospha-palladacycles in non-aqueous ionic liquids. J Organomet Chem 572:141–145
Böhm VPW, Herrmann WA (2000) Coordination chemistry and mechanisms of metal-catalyzed C–C coupling reactions, part 12 nonaqueous ionic liquids: superior reaction media for the catalytic Heck-vinylation of chloroarenes. Chem Eur J 6:1017–1025
Calò V, Nacci A, Lopez L, Mannarini N (2000) Heck reaction in ionic liquids catalyzed by a Pd–benzothiazole carbene complex. Tetrahedron Lett 41:8973–8976
Bouquillon S, Gauchegui B, Estrine B, Hénin F, Muzart J (2001) Heck arylation of allylic alcohols in molten salts. J Organomet Chem 634:153–156
Reetz MT, Breinbauer R, Wanninger K (1996) Suzuki and heck reactions catalyzed by preformed palladium clusters and palladium/nickel bimetallic clusters. Tetrahedron Lett 37:4499–4502
Reetz MT, Lohmer G (1996) Propylene carbonate stabilized nanostructured palladium clusters as catalysts in Heck reactions. Chem Commun 1921–1922
Reetz MT, Maase M (1999) Redox-controlled size-selective fabrication of nanostructured transition metal colloids. Adv Mater 11:773–777
Reetz MT, Westermann E (2000) Phosphane-free palladium-catalyzed coupling reactions: the decisive role of Pd nanoparticles. Angew Chem Int Ed Engl 39:165–168
Trzeciak AM, Ciunik Z, Ziołkowski JJ (2002) Synthesis of palladium benzyl complexes from the reaction of PdCl2[P(OPh)3]2 with benzyl bromide and triethylamine: important intermediates in catalytic carbonylation. Organometallics 21:132–137
Battistuzzi G, Cacchi S, Fabrizi G (2002) A molten n-Bu4NOAc/n-Bu4NBr mixture as an efficient medium for the stereoselective synthesis of (E)- and (Z)-3,3-diarylacrylates. Synlett 439–442
Calò V, Nacci A, Monopoli A, Laera S, Cioffi N (2003) Pd nanoparticles catalyzed stereospecific synthesis of β-aryl cinnamic esters in ionic liquids. J Org Chem 68:2929–2933
Moreno-Mañas M, Pleixats R (2003) Formation of carbon–carbon bonds under catalysis by transition-metal nanoparticles. Acc Chem Res 36:638–643
Calò V, Nacci A, Monopoli A, Detomaso A, Iliade P (2003) Pd nanoparticle catalyzed heck arylation of 1,2-disubstituted alkenes in ionic liquids study on factors affecting the regioselectivity of the coupling process. Organometallics 22:4193–4197
Gniewek A, Trzeciak AM, Ziołkowski JJ, Kepinski L, Wrzyszcz J, Tylus W (2005) Pd-PVP colloid as catalyst for Heck and carbonylation reactions: TEM and XPS studies. J Catal 229:332–343
Calò V, Nacci A, Monopoli A, Cotugno P (2009) Heck ractions with palladium nanoparticles in ionic liquids: coupling of aryl chlorides with deactivated olefins. Angew Chem Int Ed 48:6101–6103
Cotugno P, Monopoli A, Ciminale F, Cioffi N, Nacci A (2012) Pd nanoparticle catalysed one-pot sequential Heck and Suzuki couplings of bromo-chloroarenes in ionic liquids and water. Org Biomol Chem 10:808–813
Carmichael AJ, Earle MJ, Holbrey JD, Mc Cormac PB, Seddon KR (1999) The Heck reaction in ionic liquids: a multiphasic catalyst system. Org Lett 1:997–1000
Xu L, Chen W, Xiao J (2000) Heck reaction in ionic liquids and the in situ identification of N-heterocyclic carbene complexes of palladium. Organometallics 19:1123–1127
Mo J, Xu L, Xiao J (2005) Ionic liquid promoted, highly regioselective Heck arylation of electron-rich olefins by aryl halides. J Am Chem Soc 127:751–760
Mo J, Xiao J (2006) The Heck reaction of electron-rich olefins with regiocontrol by hydrogen-bond donors. Angew Chem Int Ed 45:4152–4157
Wojtkówa W, Trzeciak AM, Choukroun R, Pellegatta JL (2004) Pd colloid-catalyzed methoxycarbonylation of iodobenzene in ionic liquids. J Mol Catal A: Chem 224:81–86
Deshmukh RR, Rajagopal R, Srinivasan KV (2001) Ultrasound promoted C–C bond formation: Heck reaction at ambient conditions in room temperature ionic liquids. Chem Commun 1544–1545
Cassol CC, Umpierre AP, Machado G, Wolke SI, Dupont J (2005) The role of Pd nanoparticles in ionic liquid in the Heck reaction. J Am Chem Soc 127:3298–3299
Consorti CS, Flores FR, Dupont J (2005) Kinetics and mechanistic aspects of the Heck reaction promoted by a CN-palladacycle. J Am Chem Soc 127:12054–12065
Scholten JD, Leal BC, Dupont J (2012) Transition metal nanoparticle catalysis in ionic liquids. ACS Catal 2:184–200
Gaikwad AV, Holuigue A, Thathagar MB, ten Elshof JE, Rothenberg G (2007) Ion- and atom-leaching mechanisms from palladium nanoparticles in cross-coupling reactions. Chem Eur J 13:6908–6913
Thathagar MB, ten Elshof JE, Rothenberg G (2006) Pd nanoclusters in CC coupling reactions: proof of leaching. Angew Chem Int Ed 45:2886–2890
Kumar R, Shard A, Bharti R, Thopate Y, Sinha AK (2012) Palladium-catalyzed dehydrative heck olefination of secondary aryl alcohols in ionic liquids: towards a waste-free strategy for tandem synthesis of stilbenoids. Angew Chem Int Ed 51:2636–2639
Wan Q-X, Liu Y (2009) The ionic palladium porphyrin as a highly efficient and recyclable catalyst for the heck reaction in solution under aerobic conditions. Catal Lett 128:487–492
Hagiwara H, Shimizu Y, Hoshi T, Suzuki T, Ando M, Ohkubo K, Yokoyama C (2001) Heterogeneous heck reaction catalyzed by Pd/C in ionic liquid. Tetrahedron Lett 42:4349–4351
Choudary BM, Madhi S, Chowdari NS, Kantam ML, Sreedhar B (2002) Layered double hydroxide supported nanopalladium catalyst for Heck-, Suzuki-, Sonogashira-, and stille-type coupling reactions of chloroarenes. J Am Chem Soc 124:14127–14136
Calò V, Nacci A, Monopoli A, Fornaro A, Sabbatini L, Cioffi N, Ditaranto N (2004) Heck reaction catalyzed by nanosized palladium on chitosan in ionic liquids. Organometallics 23:5154–5158
Lu X, Xie J, Chen B, Han J, She X, Pan X (2004) Pd/C-catalyzed Heck reaction in ionic liquid accelerated by microwave heating. Tetrahedron Lett 45:809–811
Kabachii LA, Aslanov YA, Kochev SY, Romanovsky BV, Valetsky PM, Volkov VV, Yatsenko AV, Zakharov VN (2008) Mesoporous soot-supported palladium as a heterogeneous catalyst for the Heck reaction in ionic liquids. Mendeleev Commun 18:334–335
Ma X, Zhou Y, Zhang J, Zhu A, Jiang T, Han B (2008) Solvent-free Heck reaction catalyzed by a recyclable Pd catalyst supported on SBA-15 via an ionic liquid. Green Chem 10:59–66
Dighe MG, Degani MS (2011) Microwave-assisted ligand-free, base-free Heck reactions in a task-specific imidazolium ionic liquid. ARKIVOC xi:189–197
Xiao JC, Twamley B, Shreeve JM (2004) An ionic liquid-coordinated palladium complex: a highly efficient and recyclable catalyst for the Heck reaction. Org Lett 6:3845–3847
Wang R, Piekarski MP, Shreeve J (2006) New types of pyrazolyl-functionalized 2-methylimidazolium-based ionic liquids and their palladium(II) complexes: highly efficient, recyclable catalysts for C–C coupling reactions. Org Biomol Chem 4:1878–1886
Wang R, Zeng Z, Twamley B, Piekarski MM, Shreeve JM (2007) Synthesis and characterization of pyrazolyl-functionalized imidazolium-based ionic liquids and hemilabile palladium(II) carbene complex catalyzed Heck reaction. Eur J Org Chem 655–661
Wang R, Twamley B, Shreeve JM (2006) A highly efficient, recyclable catalyst for C–C coupling reactions in ionic liquids: pyrazolyl-functionalized N-heterocyclic carbene complex of palladium(II). J Org Chem 71:426–429
Jin CM, Twamley B, Shreeve J (2005) Low-melting dialkyl- and bis(polyfluoroalkyl)-substituted 1,1′-methylene-bis(imidazolium) and 1,1′-methylenebis (1,2,4-triazolium) bis (trifluoromethanesulfonyl) amides: ionic liquids leading to bis(N-heterocyclic carbene) complexes of palladium. Organometallics 24:3020–3023
Wang R, Jin CM, Twamley B, Shreeve JM (2006) Syntheses and characterization of unsymmetric dicationic salts incorporating imidazolium and triazolium functionalities. Inorg Chem 45:6396–6403
Iranpoor N, Firouzabadi H, Azadi R (2007) An imidazolium-based phosphinite ionic liquid (IL-OPPh2) as a reusable reaction medium and PdII ligand in Heck reactions of aryl halides with styrene and n-butyl acrylate. Eur J Org Chem 2197–2201
Fei Z, Zhao D, Pieraccini D, Ang WH, Geldbach TJ, Scopelliti R, Chiappe C, Dyson PJ (2007) Development of nitrile-functionalized ionic liquids for C − C coupling reactions: implication of carbene and nanoparticle catalysts. Organometallics 26:1588–1598
Bellina F, Bertoli A, Melai B, Scalesse F, Signori F, Chiappe C (2009) Synthesis and properties of glycerylimidazolium based ionic liquids: a promising class of task-specific ionic liquids. Green Chem 11:622–629
Cai Y, Liu Y (2009) Efficient palladium-catalyzed Heck reactions mediated by diol-functionalized imidzolium ionic liquids. Cat Comm 10:1390–1393
Wang L, Li H, Li P (2008) Task-specific ionic liquid as base, ligand and reaction medium for the palladium-catalyzed Heck reaction. Tetrahedron 65:364–368
Li S, Li Y, Xie H, Zhang S, Xu J (2006) Bronsted guanidine acid–base ionic liquids: novel reaction media for the palladium catalyzed Heck reaction. Org Lett 8:391–394
Wan QX, Liu Y, Lu Y, Li M, Wu HH (2008) Palladium-catalyzed heck reaction in the multi-functionalized ionic liquid compositions. Catal Lett 121:331–336
Riisager A, Wasserscheid P, Hal R, Fehrmann R (2003) Continuous fixed-bed gas-phase hydroformylation using supported ionic liquid-phase (SILP) Rh catalysts. J Catal 219:452–455
Riisager A, Fehrmann R, Haumann M, Wasserscheid P (2006) Supported ionic liquids: versatile reaction and separation media. Topics Catal 40:91–102
Werner S, Szesni N, Kaiser M, Haumann M, Wasserscheid P (2012) A scalable preparation method for SILP and SCILL ionic liquid thin-film materials. Chem Eng Technol 35:1962–1967
Kernchen U, Etzold B, Korth W, Jess A (2007) Solid catalyst with ionic liquid layer (SCILL) – a new concept to improve selectivity illustrated by hydrogenation of cyclooctadiene. Chem Eng Technol 30:985–994
Steinruck HP, Libuda J, Wasserscheid P, Cremer T, Kolbeck C, Laurin M, Maier F, Sobota M, Schulz PS, Stark M (2011) Surface science and model catalysis with ionic liquid-modified materials. Adv Mater 23:2571–2587
Sobota M, Happel M, Amende M, Paape N, Wasserscheid P, Laurin M, Libuda J (2011) Ligand effects in SCILL model systems: site-specific interactions with Pt and Pd nanoparticles. Adv Mater 23:2617–2621
Wan L, Zhang Y, Xie C, Wang Y (2005) PEG-supported imidazolium chloride: a highly efficient and reusable reaction medium for the heck reaction. Synlett 12:1861–1864
Burguete MI, García-Verdugo E, Garcia-Villar I, Gelat F, Licence P, Luis SV, Sans V (2010) Pd catalysts immobilized onto gel-supported ionic liquid-like phases (g-SILLPs): a remarkable effect of the nature of the support. J Catal 269:150–160
Liu G, Hou M, Song J, Jiang T, Fan H, Zhang Z, Han B (2010) Immobilization of Pd nanoparticles with functional ionic liquid grafted onto cross-linked polymer for solvent-free heck reaction. Green Chem 12:65–69
Shi X, Han X, Ma W, Fan J, Wei J (2012) A PdCl2–ionic liquid brush assembly: an efficient and reusable catalyst for Mizoroki–Heck reaction in neat water. Appl Organom Chem 26:16–20
Brun N, Hesemann P, Laurent G, Sanchez C, Birot M, Deleuze H, Backov R (2013) Macrocellular Pd@ionic liquid@organo-Si(HIPE) heterogeneous catalysts and their use for Heck coupling reactions. New J Chem 37:157–168
Payagala T, Armstrong DW (2012) Chiral ionic liquids: a compendium of syntheses and applications (2005–2012). Chirality 24:17–53
Prechtl MHG, Scholten JD, Neto BAD, Dupont J (2009) Application of chiral ionic liquids for asymmetric induction in catalysis. Curr Org Chem 13:1259–1277
Gayet F, Marty J-D, Lauth de Viguerie N (2008) Palladate salts from ionic liquids as catalysts in the Heck reaction. ARKIVOC xvii:61–76
Kiss L, Kurtán T, Antus S, Brunner H (2003) Further insight into the mechanism of Heck oxyarylation in the presence of chiral ligands. ARKIVOC v:69–76
Pastre JC, Génisson Y, Saffon N, Dandurand J, Correia CRD (2010) Synthesis of novel room temperature chiral ionic liquids: application as reaction media for the heck arylation of aza-endocyclic acrylates. J Braz Chem Soc 21:821–836
Roszak R, Trzeciak AM, Pernak J, Borucka N (2011) Effect of chiral ionic liquids on palladium-catalyzed Heck arylation of 2,3-dihydrofuran. Appl Catal A 148:409–410
Morel A, Silarska E, Trzeciak AM, Pernak J (2013) Palladium-catalyzed asymmetric Heck arylation of 2,3-dihydrofuran – effect of prolinate salts. Dalton Trans 42:1215–1222
Calò V, Nacci A, Monopoli A, Ferola V (2007) Palladium-catalyzed Heck arylations of allyl alcohols in ionic liquids: remarkable base effect on the selectivity. J Org Chem 72:2596–2601
Lee JW, Shin JY, Chun YS, Jang HB, Song CE, Lee S (2010) Toward understanding the origin of positive effects of ionic liquids on catalysis: formation of more reactive catalysts and stabilization of reactive intermediates and transition states in ionic liquids. Acc Chem Res 43:985–994
Ruan J, Xiao J (2011) From α-arylation of olefins to acylation with aldehydes: a journey in regiocontrol of the Heck reaction. Acc Chem Res 44:614–626
Shaw BL (1998) Speculations on new mechanisms for Heck reactions. New J Chem 22:77
Amatore C, Jutand A (2000) Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions. Acc Chem Res 33:314–321
de Vries J G (2006) A unifying mechanism for all high-temperature Heck reactions. The role of palladium colloids and anionic species. Dalton Trans 421–429
Shaw BL (1998) Chelating diphosphine–palladium(II) dihalides, outstandingly good catalysts for Heck reactions of aryl halides. Chem Commun 1863–1864
Phan NTS, Van Der Sluys M, Jones CW (2006) On the nature of the active species in palladium catalyzed Mizoroki–Heck and Suzuki–Miyaura couplings – homogeneous or heterogeneous catalysis, a critical review. Adv Synth Catal 348:609–679
Miyaura N, Suzuki A (1995) Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev 95:2457–2483
Christopher JM, Paul JS, Welton T (2000) Palladium catalysed Suzuki cross-coupling reactions in ambient temperature ionic liquids. Chem Commun 1249–1250
Miyaura N, Yanagi T, Suzuki A (1981) The palladium-catalyzed cross-coupling reaction of phenylboronic acid with haloarenes in the presence of bases. Synth Commun 11:513–519
McLachlan F, Mathews CJ, Smith PJ, Welton T (2003) Palladium-catalyzed Suzuki cross-coupling reactions in ambient temperature ionic liquids: evidence for the importance of palladium imidazolylidene complexes. Organometallics 22:5350–5357
Rajagopal R, Jarikote DV, Srinivasan KV (2002) Ultrasound promoted Suzuki cross-coupling reactions in ionic liquid at ambient conditions. Chem Commun 616–617
McNulty J, Capretta A, Wilson J, Dyck J, Adjabeng G, Robertson A (2002) Suzuki cross-coupling reactions of aryl halides in phosphonium salt ionic liquid under mild conditions. Chem Commun 1986–1987
Miao W, Chan TH (2003) Exploration of ionic liquids as soluble supports for organic synthesis demonstration with a Suzuki coupling reaction. Org Lett 5:5003–5005
Zhao D, Fei Z, Geldbach TJ, Scopelliti R, Dyson PJ (2004) Nitrile-functionalized pyridinium ionic liquids: synthesis, characterization, and their application in carbon–carbon coupling reactions. J Am Chem Soc 126:15876–15882
Albrecht M, Stoeckli-Evans H (2005) Catalytically active palladium pyridylidene complexes: pyridinium ionic liquids as N-heterocyclic carbene precursors. Chem Commun 4705–4707
Gallo V, Mastrorilli P, Nobile CF, Paolillo R, Taccardi N (2005) Ionic liquids as reaction media for palladium-catalysed cross-coupling of Aryldiazonium tetrafluoroborates with potassium organotrifluoroborates. Eur J Inorg Chem 582–588
Yan N, Yang X, Fei Z, Li Y, Kou Y, Dyson PJ (2009) Solvent-enhanced coupling of sterically hindered reagents and aryl chlorides using functionalized ionic liquids. Organometallics 28:937–939
Lombardo M, Chiarucci M, Trombini C (2009) A recyclable triethylammonium ion-tagged diphenylphosphine palladium complex for the Suzuki–Miyaura reaction in ionic liquids. Green Chem 11:574–579
Escarcega-Bobadilla MV, Teuma E, Masdeu-Bulto AM, Gomez M (2011) New bicyclic phosphorous ligands: synthesis, structure and catalytic applications in ionic liquids. Tetrahedron 67:421–428
Jin M-J, Taher A, Kang H-J, Choi M, Ryoo R (2009) Palladium acetate immobilized in a hierarchical MFI zeolite-supported ionic liquid: a highly active and recyclable catalyst for Suzuki reaction in water. Green Chem 11:309–313
Wei J-F, Jiao J, Feng J-J, Lv J, Zhang X-R, Shi X-Y, Chen Z-G (2009) PdEDTA held in an ionic liquid brush as a highly efficient and reusable catalyst for Suzuki reactions in water. J Org Chem 74:6283–6286
Calò V, Nacci A, Monopoli A, Montingelli F (2005) Pd nanoparticles as efficient catalysts for Suzuki and stille coupling reactions of aryl halides in ionic liquids. J Org Chem 70:6040–6044
Fernandez F, Cordero B, Durand J, Muller G, Malbosc F, Kihn Y, Teuma E, Gomez M (2007) Palladium catalyzed Suzuki C–C couplings in an ionic liquid: nanoparticles responsible for the catalytic activity. Dalton Trans 5572–5581
Durand J, Teuma E, Malbosc F, Kihn Y, Gomez M (2008) Palladium nanoparticles immobilized in ionic liquid: an outstanding catalyst for the Suzuki C–C coupling. Catal Commun 9:273–275
Oda Y, Hirano K, Yoshii K, Kuwabata S, Torimoto T, Miura M (2010) Palladium nanoparticles in ionic liquid by sputter deposition as catalysts for Suzuki–Miyaura coupling in water. Chem Lett 39(10):1069–1071
Yu Y, Hu T, Chen X, Xu K, Zhang J, Huang J (2012) Pd nanoparticles on a porous ionic copolymer: a highly active and recyclable catalyst for Suzuki–Miyaura reaction under air in water. Chem Commun 47:3592–3594
Deshmukh KM, Qureshi ZS, Bhatte KD, Venkatesan KA, Srinivasan TG, Rao PRV, Bhanage BM (2012) One-pot electrochemical synthesis of palladium nanoparticles and their application in the Suzuki reaction. New J Chem 35:2747–2751
Planellas M, Pleixats R, Shafir A (2012) Palladium nanoparticles in Suzuki cross-couplings: tapping into the potential of tris-imidazolium salts for nanoparticle stabilization. Adv Synt Catal 354:651–662
Song H, Yan N, Fei Z, Kilpin KJ, Scopelliti R, Li X, Dyson PJ (2012) Evaluation of ionic liquid soluble imidazolium tetrachloropalladate pre-catalysts in Suzuki coupling reactions. Catal Today 183:172–177
Wang J, Xu B, Sun H, Song G (2013) Palladium nanoparticles supported on functional ionic liquid modified magnetic nanoparticles as recyclable catalyst for room temperature Suzuki reaction. Tetrahedron Lett 54:238–241
Stille JK (1986) The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles. Angew Chem Int Ed Engl 25:508–524
Handy ST, Zhang X (2001) Organic synthesis in ionic liquids: the stille coupling. Org Lett 3:233–236
Cui YG, Biondi I, Chaubey M, Yang X, Fei ZF, Scopelliti R, Hartinger CG, Li YD, Chiappe C, Dyson PJ (2010) Nitrile-functionalized pyrrolidinium ionic liquids as solvents for cross-coupling reactions involving in situ generated nanoparticle catalyst reservoirs. Phys Chem Chem Phys 12:1834–1841
Chiappe C, Pieraccini D, Zhao D, Fei Z, Dyson PJ (2006) Remarkable anion and cation effects on stille reactions in functionalised ionic liquids. Adv Synth Catal 348:68–74
Vitz J, Mac DH, Legoupy S (2007) Ionic liquid supported tin reagents for stille cross coupling reactions. Green Chem 9:431–433
Sonogashira K (2002) In: Negishi E (ed) Handbook of organopalladium chemistry for organic synthesis. Wiley, New York
Chinchilla R, Najera C (2007) The Sonogashira reaction: a booming methodology in synthetic organic chemistry. Chem Rev 107:874–922
Fukuyama T, Shinmen M, Nishitani S, Sato M, Ryu I (2002) A copper-free Sonogashira coupling reaction in ionic liquids and its application to a microflow system for efficient catalyst recycling. Org Lett 4:1691–1694
Kmentová I, Gotov B, Gajda V, Toma S (2003) The Sonogashira reaction in ionic liquids. Monatsh Chem 134:545–547
Park B, Alper H (2004) Recyclable Sonogashira coupling reactions in an ionic liquid, effected in the absence of both a copper salt and a phosphine. Chem Commun 1306–1307
Corma A, Garcia H, Leyva A (2005) Comparison between polyethylenglycol and imidazolium ionic liquids as solvents for developing a homogeneous and reusable palladium catalytic system for the Suzuki and Sonogashira coupling. Tetrahedron 61:9848–9854
Li Y, Zhang J, Wang W, Miao Q, She X, Pan X (2005) Efficient synthesis of tribenzohexadehydro[12]annulene and its derivatives in the ionic liquid. J Org Chem 70:3285–3287
Sans V, Trzeciak AM, Luis S, Ziółkowski JJ (2006) PdCl2(P(OPh)3)2 catalyzed coupling and carbonylative coupling of phenylacetylenes with aryl iodides in organic solvents and in ionic liquids. Catal Lett 109:37–41
Blaszczyk I, Trzeciak AM, Ziolkowski JJ (2009) Catalytic activity of Pd(II) complexes with triphenylphosphito ligands in the Sonogashira reaction in ionic liquid media. Catal Lett 133:262–266
Rahman MT, Fukuyama T, Kamata N, Sato M, Ryu I (2006) Low pressure Pd-catalyzed carbonylation in an ionic liquid using a multiphase microflow system. Chem Commun 2236–2238
Rahman MT, Fukuyama T, Ryu I, Suzuki K, Yonemura K, Hughes PF, Nokihara K (2006) High throughput evaluation of the production of substituted acetylenes by the Sonogashira reaction followed by the Mizoroki–Heck reaction in ionic liquids, in situ, using a novel array reactor. Tetrahedron Lett 47:2703–2706
Hierso J-C, Boudon J, Picquet M, Meunier P (2007) The first catalytic method for Heck alkynylation of unactivated aryl bromides (copper-free Sonogashira) in an ionic liquid: 1 mol-% palladium/triphenylphosphane/pyrrolidine in [BMIM][BF4] as a simple, inexpensive and recyclable system. Eur J Org Chem 583–587
de Lima PG, Antunes OAC (2008) Copper-free Sonogashira cross coupling in ionic liquids. Tetrahedron Lett 49:2506–2509
Harjani JR, Abraham TJ, Gomez AT, Garcia MT, Singer RD, Scammells PJ (2010) Sonogashira coupling reactions in biodegradable ionic liquids derived from nicotinic acid. Green Chem 12:650–655
Iranpoor N, Firouzabadi H, Ahmadi Y (2012) Carboxylate-based, room-temperature ionic liquids as efficient media for palladium-catalyzed homocoupling and Sonogashira–Hagihara reactions of aryl halides. Eur J Org Chem 2:305–311
Zhang J, Đaković M, Popović Z, Wu H, Liu Y (2012) A functionalized ionic liquid containing phosphine-ligated palladium complex for the Sonogashira reactions under aerobic and CuI-free conditions. Catal Commun 17:160–163
Fukuyama T, Rahman MT, Maetani S, Ryu I (2011) Copper-free Sonogashira coupling reaction in phosphonium amino acid ionic liquids. Chem Lett 40:1027–1029
Pachon LD, Elsevier CJ, Rothenberg G (2006) Electroreductive palladium-catalysed Ullmann reactions in ionic liquids: scope and mechanism. Adv Synt Catal 348:1705–1710
Calo V, Nacci A, Monopoli A, Cotugno P (2009) Palladium-nanoparticle-catalysed Ullmann reactions in ionic liquids with aldehydes as the reductants: scope and mechanism. Chem Eur J 15:1272–1279
Monopoli A, Calò V, Ciminale F, Cotugno P, Angelici C, Cioffi N, Nacci A (2010) Glucose as clean and renewable reductant in the Pd-nanoparticles-catalyzed reductive homocoupling of bromo- and chloro-arenes in water. J Org Chem 75:3908–3911
Monopoli A, Nacci A, Calò V, Ciminale F, Cotugno P, Mangone A, Giannossa LC, Azzone P, Cioffi N (2010) Palladium/zirconium oxide nanocomposite as a highly recyclable catalyst for C–C coupling reactions in water. Molecules 15:4511–4525
Cheng J, Tang L, Xu J (2010) An economical, green pathway to biaryls: palladium nanoparticles catalyzed Ullmann reaction in ionic liquid/supercritical carbon dioxide system. Adv Synt Catal 352:3275–3286
Cheng J, Zhang G, Du J, Tang L, Xu J, Li J (2011) New role of graphene oxide as active hydrogen donor in the recyclable palladium nanoparticles catalyzed Ullmann reaction in environmental friendly ionic liquid/supercritical carbon dioxide system. J Mat Chem 21:3485–3494
Negishi E, King AO, Okukado N (1977) J Org Chem 42:1821–1823
Negishi E (1982) Palladium- or nickel-catalyzed cross coupling a new selective method for carbon–carbon bond formation. Acc Chem Res 15:340–348
Sirieix J, Oberger M, Betzemeier B, Knochel P (2000) Palladium catalyzed cross-couplings of organozincs in ionic liquids. Synlett 1613–1615
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Mastrorilli, P., Monopoli, A., Dell’Anna, M.M., Latronico, M., Cotugno, P., Nacci, A. (2013). Ionic Liquids in Palladium-Catalyzed Cross-Coupling Reactions. In: Dupont, J., Kollár, L. (eds) Ionic Liquids (ILs) in Organometallic Catalysis. Topics in Organometallic Chemistry, vol 51. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_2013_64
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