Abstract
This review summarizes recent advances in the field of aryl radical chemistry. In particular, modern developments of the well-known Meerwein, Pschorr, and Gomberg–Bachmann reactions are presented along with new applications in natural product syntheses. Among the methods for the generation of aryl radicals, tin hydrides play a predominant role, but more and more attractive and promising alternatives are beginning to emerge.
Keywords
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- AIBN:
-
Azo-bis(isobutyronitrile)
- PTGB:
-
Phase-transfer Gomberg–Bachmann
- TEMPO:
-
2,2,6,6-Tetramethylpiperidine-1-oxyl (radical)
References
Griess P (1866) Justus Liebig Ann 137:39
Gomberg M (1900) J Am Chem Soc 22:757
Sandmeyer T (1884) Chem Ber 17:1633
Pschorr R (1896) Chem Ber 29:496
Gomberg M, Bachmann WE (1924) J Am Chem Soc 46:2339
Meerwein H, Büchner E, Emster Kv (1939) J Prakt Chem 152:237
Galli C (1988) Chem Rev 88:765
Walters WA (1967) The chemistry of free radicals. Wiley, Boca Raton
Zollinger H (1973) Acc Chem Res 6:335
Cohen T, Lewarchik RJ, Tarino JZ (1974) J Am Chem Soc 96:7753
Cohen T, Dietz AG, Miser JR (1977) J Org Chem 42:2053
Kerk GM vd (1957) J Appl Chem 356
Studer A, Bossart M (2001) In: Renaud P, Sibi M (eds) Radicals in organic synthesis, 2nd edn. Wiley-VCH, Weinheim
Bowman WR, Storey JMD (2007) Chem Soc Rev 36:1803
Vaillard SE, Schulte B, Studer A (2009) In: Ackermann L (ed) Modern arylation methods. Wiley-VCH, Weinheim
Majumdar KC, Basu PK, Mukhopadhyay PP (2005) Tetrahedron 61:10603
Majumdar KC, Basu PK, Chattopadhyay SK (2007) Tetrahedron 63:793
Beckwith ALJ, Meijs GF (1987) J Org Chem 52:1922
Bhandal H, Patel VF, Pattenden G, Russell JJ (1990) J Chem Soc Perkin Trans 1 10:2691
Meijs GF, Beckwith ALJ (1986) J Am Chem Soc 108:5890
Beckwith ALJ, Gara WB (1975) J Chem Soc Perkin Trans 2 795
Beckwith ALJ, Meijs GF (1981) J Chem Soc Chem Commun 3:136
Petrillo G, Novi M, Garbarino G, Filiberti M (1988) Tetrahedron Lett 29:4185
Fletcher RJ, Lampard C, Murphy JA, Lewis N (1995) J Chem Soc Perkin Trans 1 6:623
Koizumi T, Bashir N, Murphy JA (1997) Tetrahedron Lett 38:7635
Koizumi T, Bashir N, Kennedy AR, Murphy JA (1999) J Chem Soc Perkin Trans 1 24:3637
Togo H, Kikuchi O (1988) Tetrahedron Lett 29:4133
Liu Y, Schwartz J (1995) Tetrahedron 51:4471
Perchyonok VT, Tuck KL, Langford SJ, Hearn MW (2008) Tetrahedron Lett 49:4777
Abeywickrema AN, Beckwith ALJ (1986) Tetrahedron Lett 27:109
Boivin J, Camara J, Zard SZ (1992) J Am Chem Soc 114:7909
Totleben MJ, Curran DP, Wipf P (1992) J Org Chem 57:1740
Curran DP, Totleben MJ (1992) J Am Chem Soc 114:6050
Molander GA, Harring LS (1990) J Org Chem 55:6171
Patel VF, Pattenden G (1987) Tetrahedron Lett 28:1451
Martin GC, Murphy JA, Smith CR (2000) Tetrahedron Lett 41:1833
Mahesh M, Murphy JA, LeStrat F, Wessel HP (2009) Beilstein J Org Chem 5(1)
Murphy JA, Khan TA, Zhou S, Thomson DW, Mahesh M (2005) Angew Chem Int Ed 44:1356
Fukuyama T, Kobayashi M, Rahman MT, Kamata N, Ryu I (2008) Org Lett 10:533
Alabugin IV, Manoharan M (2005) J Am Chem Soc 127:12583
Ishibashi H, Kobayashi T, Nakashima S, Tamura O (2000) J Org Chem 65:9022
Curran D, Fairweather M (2003) J Org Chem 68:2972
Kamimura A, Ishihara Y, So M, Hayashi T (2009) Tetrahedron Lett 50:1727
De la Fuente MC, Dominguez D (2007) J Org Chem 72:8804
Navarro-Vázquez A, Garcia A, Dominguez D (2002) J Org Chem 67:3213
Petit M, Lapierre AJB, Curran DP (2005) J Am Chem Soc 127:14994
Petit M, Geib SJ, Curran DP (2004) Tetrahedron 60:7543
Majumdar KC, Alam S (2006) Org Lett 8:4059
Dandapani S, Duduta M, Panek JS, Porco JA Jr (2007) Org Lett 9:3849
Sato A, Yorimitsu H, Oshima K (2006) J Am Chem Soc 128:4240
Vaillard SE, Mueck-Lichtenfeld C, Grimme S, Studer A (2007) Angew Chem Int Ed 46:6533
Beckwith ALJ, Wang S, Warkentin J (1987) J Am Chem Soc 109:5289
Beak P, Park YS, Reif LA, Liu C (1994) J Org Chem 59:7410
Viswanathan R, Prabhakaran EN, Plotkin MA, Johnston JN (2003) J Am Chem Soc 125:163
McClure CK, Kiessling AJ, Link JS (1998) Tetrahedron 54:7121
Tomaszewski MJ, Warkentin J (1992) Tetrahedron Lett 33:2123
Johnston JN, Plotkin MA, Viswanathan R, Prabhakaran EN (2001) Org Lett 3:109
Viswanathan R, Smith CR, Prabhakaran EN, Johnston JN (2008) J Org Chem 73:3040
Coulomb J, Certal V, Fentserbank L, Lacôte E, Malacria M (2006) Angew Chem Int Ed 45:633
Benati L, Leardini R, Minozzi M, Nanni D, Spagnolo P, Strazzari S, Zanardi G (2002) Org Lett 4:3079
Oii T, Furuya M, Sakai D, Maruoka K (2001) Adv Synth Catal 343:166
Carta P, Puljic N, Robert C, Dhimane AL, Fensterbank L, Lacôte E, Malacria M (2007) Org Lett 9:1061
Hilton ST, Ho TCT, Pljevaljcic G, Schulte M, Jones K (2001) Chem Commun 2:209
Rey V, Pierini AB, Penénory AB (2009) J Org Chem 74:1223
Amrein S, Bossart M, Vasella T, Studer A (2000) J Org Chem 65:4281
Schiesser CH, Sutej K (1992) Tetrahedron Lett 33:5137
Engman L, Laws MJ, Malmström J, Schiesser CH, Zugaro LM (1999) J Org Chem 64:6764
Laws MJ, Schiesser CH (1997) Tetrahedron Lett 38:8429
Bowman WR, Fletcher AJ, Potts GBS (2002) J Chem Soc Perkin Trans 1 2747
Ikeda M, Ohtani S, Sato T, Ishibashi H (1998) Synthesis 12:1803
Patro B, Murphy JA (2000) Org Lett 2:3599
Zhou SZ, Bommezijn S, Murphy JA (2002) Org Lett 4:443
Rivkin A, Nagashina T, Curran DP (2003) Org Lett 5:419
Li F, Castle SL (2007) Org Lett 9:4033
Li F, Tartakoff SS, Castle SL (2009) J Org Chem 74:9082
Rigby JH, Qabar M (1991) J Am Chem Soc 113:8976
Rigby JH, Mateo ME (1996) Tetrahedron 52:10569
Schultz AG, Holoboski MA, Smyth MS (1993) J Am Chem Soc 115:7904
Schultz AG, Holoboski MA, Smyth MS (1996) J Am Chem Soc 118:6210
Rigby JH, Qabar MN (1993) J Org Chem 58:4473
Taniguchi T, Ishita A, Uchiyama M, Tamura O, Muraoka O, Tanabe G, Ishibashi H (2005) J Org Chem 70:1922
Taniguchi T, Iwasaki K, Uchiyama M, Tamura O, Ishibashi H (2005) Org Lett 7:4389
Tamura O, Yanagimachi T, Kobayashi T, Ishibashi H (2001) Org Lett 3:2427
Tamura O, Yanagimachi T, Ishibashi H (2003) Tetrahedron Asymmetry 14:3033
Kato I, Higashimoto M, Tamura O, Ishibashi H (2003) J Org Chem 68:7983
Orito K, Satoh Y, Nishizawa H, Harada R, Tokuda M (2000) Org Lett 2:2535
Nanni D (2001) In: Renaud P, Sibi MP (eds) Radicals in organic synthesis, 2nd edn. Wiley-VCH, Weinheim
Servais A, Azzouz M, Lopes D, Courillon C, Malacria M (2007) Angew Chem Int Ed 46:576
Kochi JK (1955) J Am Chem Soc 77:5090
Kochi JK (1955) J Am Chem Soc 77:5274
Rondestvedt CS (1976) Org React 24:225
Heinrich MR (2009), Intermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts, Chem Eur J 15:820, Copyright Wiley-VCH Verlag GmbH & Co. KGaA. Schemes 11, 13 and 16 reproduced with permission
Mastrorilli P, Nobile CF, Taccardi N (2006) Tetrahedron Lett 47:4759
Obushak ND, Matiichuk VS, Matyak RL (2003) Heterocycl Compd 39:878
Molinaro C, Mowat J, Gosselin F, O’Shea PD, Marcoux JF, Angelaud R, Davies IW (2007) J Org Chem 72:1856
Adel IA, Salami BA, Levisalles J, Rudler H (1976) Bull Soc Chim Fr 934
Citterio A, Minisci F, Albinati A, Bruckner S (1980) Tetrahedron Lett 21:2909
Citterio A, Ramperti M, Vismara E (1981) J Heterocycl Chem 18:763
Citterio A, Minisci F, Vismara E (1982) J Org Chem 47:81
Heinrich MR, Blank O, Wölfel S (2006) Org Lett 8:3323
Heinrich MR, Blank O, Wetzel A (2007) J Org Chem 72:476
Blank O, Wetzel A, Ullrich D, Heinrich MR (2008) Eur J Org Chem 18:3179
Heinrich MR, Blank O, Wetzel A (2006) Synlett 19:3352
Ganushchak NI, Grishchuk BD, Dombrovskii AV (1973) J Org Chem USSR 9:1030
Grishchuk BD, Gorbovoi PM, Ganuschak NI, Dombrovskii AV (1994) Russ Chem Rev 63:257
Heinrich MR, Kirschstein M (2006) Tetrahedron Lett 47:2115
Beckwith ALJ, Bowry VW, Ingold KU (1992) J Am Chem Soc 114:4983
Heinrich MR, Wetzel A, Kirschstein M (2007) Org Lett 9:3833
Grishchuk BD, Gorbovoi PM, Kudrik EY, Ganuschak NI, Kaspruk BI (1997) Russ J Gen Chem 67:362
Grishchuk BD, Kudrik EY, Gorbovoi PM, Ganushchak NI, Avrashkova TV (1997) Russ J Gen Chem 67:1556
Gorbovoi PM, Kudrik EY, Grishchuk BD (1998) Russ J Gen Chem 68:1132
Grishchuk BD, Kudrik EY, Gorbovoi PM, Ganushchak NI (1996) Russ J Gen Chem 66:1482
Tournier L, Zard SZ (2005) Tetrahedron Lett 46:971
Gorbovoi PM, Tulaidan GN, Grishchuk BD (2008) Russ J Gen Chem 78:133
Grishchuk BD, Baranovskii VS, Simchak RV, Tulaidan GN, Gorbovoi PM (2006) Russ J Gen Chem 76:936
Heinrich MR, Blank O, Ullrich D, Kirschstein M (2007) J Org Chem 72:9609
Benati L, Leardini R, Minozzi M, Nanni D, Spagnolo P, Zanardi G (2000) J Org Chem 65:8669
Benati L, Calestani G, Leardini R, Minozzi M, Nanni D, Spagnolo P, Strazzari S, Zanardi G (2003) J Org Chem 68:3454
Wassmundt FW, Kiesman WF (1995) J Org Chem 60:196
Ohno H, Iwasaki H, Eguchi T, Tanaka T (2004) Chem Commun 19:2228
Narasimhan NS, Aidhen IS (1988) Tetrahedron Lett 29:2987
Orito K, Uchiito S, Satoh Y, Tatsuzawa T, Harada R, Tokuda M (2000) Org Lett 2:307 and references cited therein
Rossi RA (2005) Synthetic organic photochemistry, 2nd edn. Marcel Dekker, New York
Rossi RA, Pierini AB, Peñéñory AB (2003) Chem Rev 103:71
Barolo SM, Teng X, Cuny GD, Rossi RA (2006) J Org Chem 71:8493
Donnelly S, Grimshaw J, Trocha-Grimshaw J (1994) J Chem Soc Chem Commun 18:2171 and references cited therein
Harrowven DC, Nunn MIT, Fenwick DR (2002) Tetrahedron Lett 43:7345
Harrowven DC, Guy IL, Nanson L (2006) Angew Chem Int Ed 45:2242
Moorthy JN, Samanta S (2007) J Org Chem 72:9786
Da Mata MLEN, Motherwell WB, Ujjainwalla F (1997) Tetrahedron Lett 38:137
Alcaide B, Rodriguez-Vicente A (1998) Tetrahedron Lett 39:6589
Clive DLJ, Kang S (2000) Tetrahedron Lett 41:1315
Studer A, Bossart M, Vasella T (2000) Org Lett 2:985
Hey DH, Jones GH, Perkins MJ (1971) J Chem Soc C 116
De Turiso FGL, Curran DP (2005) Org Lett 7:151
Lanza T, Leardini R, Minozzi M, Nanni D, Spagnolo P, Zanardi G (2008) Angew Chem Int Ed 47:9439
Ho TCT, Jones K (1997) Tetrahedron 53:8287
Harrowven DC, Sutton BJ, Coulton S (2002) Tetrahedron 58:3387
Flanagan SR, Harrowven DC, Bradley M (2003) Tetrahedron Lett 44:1795
Ganguly AK, Wang CH, Chan TM, Ing YH, Buevich AV (2004) Tetrahedron Lett 45:883
Allin SM, Bowman WR, Elsegood MRJ, McKee V, Karim R, Rahman SS (2005) Tetrahedron 61:2689
Harrowven DC, Sutton BJ, Coulton S (2003) Org Biomol Chem 1:4047
Escolano C, Jones K (2002) Tetrahedron 58:1453
Harrowven DC, Woodcock T, Howes PD (2005) Angew Chem Int Ed 44:3899
Beadle JR, Korzeniowski SH, Rosenberg DE, Garcia-Slanga BJ, Gokel GW (1984) J Org Chem 49:1594
Demir AS, Reis Ö, Emrullahoglu M (2003) J Org Chem 68:578
Demir AS, Reis Ö, Özgül-Karaaslan (2001) J Chem Soc Perkin Trans 1 3042
Curran DP, Keller AI (2006) J Am Chem Soc 128:13706
Chatgilialoglu C (2008) Chem Eur J 14:2310
Androsov DA, Neckers DC (2007) J Org Chem 72:1148
Kosynkin D, Bockman TM, Kochi JK (1997) J Am Chem Soc 119:4846
Petrillo G, Novi M, Dell’Erba C, Tavan C (1991) Tetrahedron 47:9297
Wetzel A, Ehrhardt V, Heinrich MR (2008) Angew Chem 120:9270; (2008) Angew Chem Int Ed 47:9130
Wetzel A, Pratsch G, Kolb R, Heinrich MR (2010) Chem Eur J 16:2547
Crich D, Patel M (2006) Tetrahedron 62:7824
Martinez-Barrasa V, De Viedma AG, Burgos C, Alvarez-Builla J (2000) Org Lett 2:3933
Núnez A, Sánchez A, Burgos C, Alvarez-Builla J (2004) Tetrahedron 60:6217
Ryu I, Kreimerman S, Araki F, Nishitani S, Oderaotoshi Y, Minakata S, Komatsu M (2002) J Am Chem Soc 124:3812
Manolikakes G, Knochel P (2009) Angew Chem Int Ed 48:205
Ford L, Jahn U (2009) Angew Chem Int Ed 48:6386
Kobayashi T, Ohmiya H, Yorimitsu H, Oshima KJ (2008) J Am Chem Soc 130:11276
Gansäuer A, Fan CA, Piestert FJ (2008) J Am Chem Soc 130:6916
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Pratsch, G., Heinrich, M.R. (2011). Modern Developments in Aryl Radical Chemistry. In: Heinrich, M., Gansäuer, A. (eds) Radicals in Synthesis III. Topics in Current Chemistry, vol 320. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2011_127
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