Abstract
The use of tridentate anionic pincer ligands in organometallic chemistry has gained considerable importance, particularly in the field of homogenous catalysis. This chapter focuses on the recent developments of anionic tridentate NNN pincer ligands from their synthesis to coordination chemistry and their applications in forming stable transition metal complexes for applications in catalytic transformations.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsAbbreviations
- ATRP:
-
Atom transfer radical polymerization
- BOPA:
-
Bis(oxazolinylphenyl)amine
- BOX:
-
Bis(oxazoline)
- BOXMI:
-
Bis(oxazolinylmethylidene)isoindoline
- BPI:
-
Bis(2-pyridylimino)isoindole
- BQA:
-
Bis(8-quinolinyl)amine
- Cbzbox:
-
Bis-oxazoline carbazole
- DIPEA:
-
Diisopropylethylamine
- DMS:
-
Dimethylsilane
- iproxpH:
-
Bis[2-(4,4-diisopropyl-4,5-dihydrooxazolyl)]pyrrole
- NHK:
-
Nozaki–Hiyama–Kishi
- PDI:
-
Polydispersity index
- pyBOX:
-
Pyridine bis(oxazoline)
- PyrrMeBOX:
-
2,5-Bis(2-oxazolinylmethyl)pyrrole
- SIPr:
-
1,3-Bis(2,6-di-i-propylphenyl)imidazolidin-2-ylidene
- TBAF:
-
Tetrabutylammonium fluoride
- thq:
-
Tetrahydroquinoline
References
van Koten G (1989) Pure Appl Chem 61:1681
Peris E, Crabtree RH (2004) Coord Chem Rev 248:2239
Morales-Morales D, Jensen CGM (2007) The chemistry of pincer compounds. Elsevier, Amsterdam
Chase PA, van Koten G (2010) The pincer ligand: its chemistry and applications (Catalytic Science), 1st edn. Imperial College Press, London
van Koten G, Milstein D (eds.) (2013) Top Organomet Chem 40
Rasappan R, Laventine D, Reiser O (2008) Coord Chem Rev 252:702
Desimoni G, Faita G, Quadrelli P (2003) Chem Rev 103:3119
Desimoni G, Faita G, Jørgensen KA (2006) Chem Rev 106:3561
Evans DA, Miller SJ, Lectka T, von Matt P (1999) J Am Chem Soc 121:7559
Thorhauge J, Roberson M, Hazell RG, Jørgensen KA (2002) Chem Eur J 8:1888
Inoue M, Suzuki T, Nakada M (2003) J Am Chem Soc 125:1140
Suzuki T, Kinoshita A, Kawada H, Nakada M (2003) Synlett 2003:570
Inoue M, Nakada M (2007) Heterocycles 72:133
Durán-Galván M, Worlikar SA, Connell BT (2010) Tetrahedron 66:7707
Britovsek GJP, Gibson VC, Hoarau OD, Spitzmesser SK, White AJP, Williams DJ (2003) Inorg Chem 42:3454
Gibson VC, Spitzmesser SK, White AJP, Williams DJ (2003) Dalton Trans 2003:2718
Barbe J-M, Habermeyer B, Khoury T, Gros CP, Richard P, Chen P, Kadish KM (2010) Three-metal coordination by novel bisporphyrin architectures. Inorg Chem 49:8929–8940
Mudadu MS, Singh AN, Thummel RP (2008) J Org Chem 73:6513
Johnson KRD, Hayes PG (2009) Organometallics 28:6352
Wang L, Cui D, Hou Z, Li W, Li Y (2011) Organometallics 30:760
Johnson KRD, Kamenz BL, Hayes PG (2014) Organometallics 33:3005
Mazet C, Gade LH (2003) Chem Eur J 9:1759
Konrad F, Lloret Fillol J, Wadepohl H, Gade LH (2009) Inorg Chem 48:8523
Ghorai D, Kumar S, Mani G (2012) Dalton Trans 41:9503
McManus HA, Guiry PJ (2002) J Org Chem 67:8566
Lu S-F, Du D-M, Zhang S-W, Xu J (2004) Tetrahedron Asymmetry 15:3433
Peters JC, Harkins SB, Brown SD, Day MW (2001) Inorg Chem 40:5083
Csok Z, Vechorkin O, Harkins SB, Scopelliti R, Hu X (2008) J Am Chem Soc 130:8156
Wanniarachchi S, Liddle BJ, Toussainta J, Lindeman SV, Bennett B, Gardinier JR (2010) Dalton Trans 39:3167
Elvidge JA, Linstead RP (1952) J Chem Soc 5000
Elvidge JA, Linstead RP (1952) J Chem Soc 1952:5008
Clark PF, Elvidge JA, Linstead PR (1953) J Chem Soc 1953:3593
Sauer DC, Melen RL, Kruck M, Gade LH (2014) Eur J Inorg Chem 2014:4715
Siegl WO (1974) Inorg Nucl Chem Lett 10:825
Siegl WO (1977) J Org Chem 42:1872
Meder MB, Gade LH (2004) Eur J Inorg Chem 2004:2716
Langlotz BK, Wadepohl H, Gade LH (2008) Angew Chem Int Ed 47:4670
Sauer DC, Wadepohl H, Gade LH (2012) Inorg Chem 51:12948
Deng Q-H, Wadepohl H, Gade LH (2001) Chem Eur J 17:14922
Robinson MA, Trotz SI, Hurley TJ (1967) Inorg Chem 6:392
Beattie JK (1988) Adv Inorg Chem 132:1
Letcher RJ, Zhang W, Bensimon C, Crutchley RJ (1993) Inorg Chim Acta 210:183
Kruck M, Sauer DC, Enders M, Wadepohl H, Gade LH (2011) Dalton Trans 40:10406
Kruck M, Wadepohl H, Enders M, Gade LH (2013) Chem Eur J 19:1599
Sauer DC, Kruck M, Wadepohl H, Enders M, Gade LH (2013) Organometallics 32:885
Deng Q-H, Wadepohl H, Gade LH (2012) J Am Chem Soc 134:2946
Puzas JP, Nakon R, Pertersen JL (1986) Inorg Chem 25:3837
Maiti D, Paul H, Chanda N, Chakraborty S, Mondal B, Puranik VG, Lahiri GK (2004) Polyhedron 23:831
Fout AR, Basuli F, Fan H, Tomaszewski J, Huffman JC, Baik M-H, Mindiola DJ (2005) Angew Chem Int Ed 45:3291
Harkins SB, Peters JC (2006) Inorg Chem 45:4316
Betley TA, Qian BA, Peters JC (2008) Inorg Chem 47:11570
Wen H-M, Wang J-Y, Li B, Zhang L-Y, Chen C-N, Chen Z-N (2013) Eur J Inorg Chem 2013:4789
Camerano JA, Sämann C, Wadepohl H, Gade LH (2011) Organometallics 30:379
Vechorkin O, Hu X (2009) Angew Chem Int Ed 48:2937
Vechorkin O, Proust V, Hu X (2009) J Am Chem Soc 131:9756
Vechorkin O, Barmaz D, Proust V, Hu X (2009) J Am Chem Soc 131:12078
Vechorkin O, Proust V, Hu X (2010) Angew Chem Int Ed 49:3061
Hu X (2011) Chem Sci 2:1867
Vechorkin O, Godinat A, Scopelliti R, Hu X (2011) Angew Chem Int Ed 50:11777
Vechorkin O, Csok Z, Scopelliti R, Hu XL (2009) Chem Eur J 15:3889
Breitenfeld J, Vechorkin O, Corminboeuf C, Scopelliti R, Hu XL (2010) Organometallics 29:3686
Breitenfeld J, Ruiz J, Wodrich MD, Hu X (2013) J Am Chem Soc 135:12004
Breitenfeld J, Wodrich MD, Hu X (2014) Organometallics 33:5708
Di Franco T, Boutin N, Hu X (2013) Synthesis 45:2949
Fürstner A (1999) Chem Rev 99:991
Wessjohann LA, Scheid G (1999) Synthesis 1999:1
Avalos M, Babiano R, Cintas P, Jiménez JL, Palacios JC (1999) Chem Soc Rev 28:169
Okude Y, Hirano S, Hiyama T, Nozaki H (1977) J Am Chem Soc 99:3179
Okude Y, Hiyama T, Nozaki H (1977) Tetrahedron Lett 18:3829
Fürstner A, Shi N (1996) J Am Chem Soc 118:12349
McManus HA, Cozzi PG, Guiry PJ (2006) Adv Synth Catal 348:551
Hargaden GC, McManus HA, Giorgio Cozzi P, Guiry PJ (2007) Org Biomol Chem 5:763
Inoue M, Nakada M (2007) J Am Chem Soc 129:4164
Inoue M, Nakada M (2004) Org Lett 6:2977
Inoue M, Nakada M (2006) Angew Chem Int Ed 45:252
Durán-Galván M, Connell BT (2010) Eur J Org Chem 2010:2445
Coeffard V, Aylward M, Guiry PJ (2009) Angew Chem Int Ed 48:9152
Olah GA, Khrisnamurti R, Prakash GKS (1991) In: Trost BM, Fleming I (eds) Comprehensive organic synthesis, vol 3. 1st edn. Pergamon, Oxford, p 293
Roberts RM, Khalaf AA (1984) Friedel–Crafts alkylation chemistry. A century of discovery. Marcel Dekker, New York
Herrera RP, Sgarzani V, Bernardi L, Ricci A (2005) Angew Chem Int Ed 44:6576
Zhuang W, Hazell RG, Jørgensen KA (2005) Org Biomol Chem 3:2566
Jia Y-X, Zhu S-F, Yang Y, Zhou Q-L (2006) J Org Chem 71:75
Lu S-F, Du D-M, Xu, J (2006) Org Lett 8:2115
Liu H, Xu J, Du D-M (2007) Org Lett 9:4725
Liu H, Lu S-F, Xu J, Du D-M (2008) Chem Asian J 3:1111
Peng J, Du D-M (2012) Eur J Org Chem 2012:4042
Jia Y, Yang W, Du D-M (2012) Org Biomol Chem 10:4739
Li C, Liu F-L, Zou Y-Q Lu L-Q, Chen J-R, Xiao W-J (2013) Synthesis 45:601
Kassube JK, Gade LH (2006) Top Organomet Chem 20:61
Liu H, Du D-M (2010) Eur J Org Chem 2010:2121
Purser S, Moore PR, Swallow S, Gouverneur V (2008) Chem Soc Rev 37:320
Tressaud A (ed) (2006) Fluorine and the environment – agrochemicals, archaeology, green chemistry & water. Adv Fluorine Sci 2
Leo A, Hansch C, Elkins D (1971) Chem Rev 71:525
Yagupolskii LM, Ilchenko AY, Kondratenko NV (1974) Russ Chem Rev 43:32
Filler R, Kobayashi Y (1982) Biomedical aspects of fluorine chemistry. Elsevier, Amsterdam
Gribkoff VK, Starrett JE, Dworetzky SI, Hewawasam P, Boissard CG, Cook DA, Frantz SW, Heman K, Hibbard JR, Huston K, Johnson G, Krishnan BS, Kinney GG, Lombardo LA, Meanwell NA, Molinoff PB, Myers RA, Moon SL, Ortiz A, Pajor L, Pieschl RL, Post-Munson DJ, Signor LJ, Srinivas N, Taber MT, Thalody G, Trojnacki JT, Wiener H, Yeleswaram K, Yeola SW (2001) Nature Med 7:471
Hewawasam P, Gribkoff VK, Pendri Y, Dworetzky SI, Meanwell NA, Martinez E, Boissard CG, Post-Munson DJ, Trojnacki JT, Yeleswaram K, Pajor LM, Knipe J, Gao Q, Perrone R, Starrett JE (2002) Bioorg Med Chem Lett 12:1023
Deng Q-H, Wadepohl H, Gade LH (2012) J Am Chem Soc 134:10769
Deng Q-H, Rettenmeier C, Wadepohl H, Gade LH (2014) Chem Eur J 20:93
Deng Q-H, Bleith T, Wadepohl H, Gade LH (2013) J Am Chem Soc 135:5356
Tan F, Xiao C, Cheng H-G, Wu W, Ding K-R, Xiao W-J (2012) Chem Asian J 7:493
Inagaki T, Ito A, Ito J-I, Nishiyama H (2010) Angew Chem Int Ed 49:9384
Nishiyama H, Furuta A (2007) Chem Commun 2007:760
Inagaki T, Phong LT, Furuta A, Ito J-i, Nishiyama H (2010) Chem Eur J 16:3090
Lu S-F, Du D-M, Xu J, Zhang S-W (2006) J Am Chem Soc 128:7418
Rosini G (1991) In: Trost BM, Heathcock CH (eds) Comprehensive organic synthesis, vol. 2. Pergamon, Oxford, pp 321–340
Ono N (2001) The nitro group in organic synthesis. Wiley-VCH, New York, Chap 3, pp 30–69
Shibasaki M, Gröger H (1999) In: Jacobsen EN, Pfaltz A, Yamamoto H (eds) Comprehensive asymmetric catalysis. Springer-Verlag, Berlin, Heidelberg, Ch. 29.3
Shibasaki M, Sasai H, Arai T (1997) Angew Chem Int Ed 36:1236
Luzzio FA (2001) Tetrahedron 57:915
Westermann B (2003) Angew Chem Int Ed 42:151
Du D-M, Lu S-F, Fang T, Xu J (2005) J Org Chem 70:3712
Breitenfeld J, Scopelliti R, Hu X (2012) Organometallics 31:2128
Rettenmeier C, Wadepohl H, Gade LH (2014) Chem Eur J 20:9657
Druliner JD, Ittel SD, Krusic PJ, Tolman CA (1982) Process for producing a mixture containing cyclohexanol and cyclohexanone from cyclohexane. US Patent 4 326 084
Tolman CA, Druliner JD, Krusic PJ, Nappa MJ, Seidel WC, Williams ID, Ittel SD (1988) J Mol Catal 48:129
Saussine L, Brazi E, Robine A, Mimoun H, Fischer J, Weiss R (1985) J Am Chem Soc 107:3534
Meder MB, Siggelkow BA, Gade LH (2004) Z Anorg Allg Chem 630:1962
Kaizer J, Pap J, Speier G, Párkányi L (2004) Z Kristallogr NCS 219:141
Csay T, Kripli B, Giorgi M, Kaizer J, Speier G (2010) Inorg Chem Commun 254:781
Kaizer J, Pap J, Speier G, Réglier M, Giorgi M (2004) Trans Met Chem 29:630
Balogh-Hergovich É, Kaizer J, Speier G, Huttner G, Jacobi A (2000) Inorg Chem 39:4224
Váradi T, Pap JS, Giorgi M, Párkányi L, Csay T, Speier G, Kaizer J (2013) Inorg Chem 52:1559
Niwa T, Nakada M (2012) J Am Chem Soc 134:13538
Siggelkow B, Meder MB, Galka CH, Gade LH (2004) Eur J Inorg Chem 2004:3424
Meder MB, Haller I, Gade LH (2005) Dalton Trans 2005:1403
Siggelkow BA, Gade LH (2005) Z Anorg Allg Chem 631:2575
Nixon TD, Ward BD (2012) Chem Commun 48:11790
Bennett SD, Pope SJA, Ward BD (2013) Chem Commun 49:6072
Bennett SD, Core BA, Blake MP, Pope SJA, Mountford P, Ward BD (2014) Dalton Trans 43:5871
Sanchez-Blanco AI, Gothelf KV, Jørgensen KA (1997) Tetrahedron Lett 38:7923
Acknowledgments
R. L. M. would like to thank the Alexander von Humboldt Foundation for a Research Fellowship.
Author information
Authors and Affiliations
Corresponding authors
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2015 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Melen, R.L., Gade, L.H. (2015). New Chemistry with Anionic NNN Pincer Ligands. In: van Koten, G., Gossage, R. (eds) The Privileged Pincer-Metal Platform: Coordination Chemistry & Applications. Topics in Organometallic Chemistry, vol 54. Springer, Cham. https://doi.org/10.1007/3418_2015_114
Download citation
DOI: https://doi.org/10.1007/3418_2015_114
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-22926-3
Online ISBN: 978-3-319-22927-0
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)