Abstract
This chapter focuses on carbon monoxide as a reagent in M–NHC catalysed reactions. The most important and popular of these reactions is hydroformylation. Unfortunately, uncertainty exists as to the identity of the active catalyst and whether the NHC is bound to the catalyst in a number of the reported reactions. Mixed bidentate NHC complexes and cobalt-based complexes provide for better stability of the catalyst. Catalysts used for hydroaminomethylation and carbonylation reactions show promise to rival traditional phosphine-based catalysts. Reports of decarbonylation are scarce, but the potential strength of the M–NHC bond is conducive to the harsh conditions required. This report will highlight, where appropriate, the potential benefits of exchanging traditional phosphorous ligands with N-heterocyclic carbenes as well as cases where the role of the NHC might need re-evaluation. A review by the author on this topic has recently appeared [1].
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References
Veige AS (2008) Polyhedron 27:3177–3189
van Leeuwen PWNM, Carmen C (2002) Rhodium catalysed hydroformylation. Kluwer, New York
Bizzari S, Blagoev M, Kishi A (2006) Chemical economics handbook. SRI Consulting, Menlo Park
Cotton FA, Wilkinson G, Murillo C, Bochmann M (1999) Advanced inorganic chemistry. Wiley, New York
Abatjoglou AG, Bryant DR (1984) Organometallics 3:932–934
Lewin M, Aizenshtat Z, Blum J (1980) J Organomet Chem 184:255–261
Garrou PE (1985) Chem Rev 85:171–185
Herrmann WA, Brossmer C, Öfele K, Beller M, Fischer H (1995) J Organomet Chem 491:C1–C4
Pruett RL, Smith JA (1969) J Org Chem 34:327–330
Herrmann WA, Fischer J, Elison M, Köcher C (1997) (Hoechst AG), DE 4447068.1 A1 (1994); EP0719758 A1; US 5.703.269
Chen AC, Ren L, Decken A, Crudden CM (2000) Organometallics 19:3459–3461
McGuinness DS, Cavell KJ (2000) Organometallics 19:4918–4920
Allen DP, Crudden CM, Calhoun LA, Wang RY (2004) J Organomet Chem 689:3203–3209
Chen AC, Allen DP, Crudden CM, Wang RY, Decken A (2005) Can J Chem 83:943–957
Widegren JA, Finke RG (2003) J Mol Cat A: Chem 198:317–341
Praetorius JM, Kotyk MW, Webb JD, Wang RY, Crudden CM (2007) Organometallics 26:1057–1061
Datt MS, Nair JJ, Otto S (2005) J Organomet Chem 690:3422–3426
Mieczynska E, Trzeciak AM, Ziolkowski JJ (1992) J Mol Cat 73:1–8
Wojciech G, Trzeciak AM, Ziolkowski JJ (2008) Organometallics 27:4131–4138
Bortenschlager M, Mayr M, Nuyken O, Buchmeiser MR (2005) J Mol Cat A: Chem 233:67–71
Bortenschlager M, Schutz J, von Preysing D, Nuyken O, Herrmann WA, Weberskirch R (2005) J Organomet Chem 690:6233–6237
Poyatos M, Uriz P, Mata JA, Claver C, Fernandez E, Peris E (2003) Organometallics 22:440–444
Jeletic MS, Jan MT, Ghiviriga I, Abboud KA, Veige AS (2009) Dalton Trans 2764–2776
Lowry RJ, Jan MT, Abboud KA, Ghiviriga I, Veige AS (2010) Polyhedron 29:553–563
Dastgir S, Coleman KS, Cowley AR, Green MLH (2006) Organometallics 25:300–306
Downing SP, Pogorzelee PG, Danopoulos AA, Cole-Hamilton DJ (2009) Eur J Inorg Chem 1816–1824
Neveling A, Julius GR, Cronje S, Esterhuysen C, Raubenheimer HG (2005) Dalton Trans 181–192
Zarka MT, Bortenschlager M, Wurst K, Nuyken O, Weberskirch R (2004) Organometallics 23:4817–4820
van Rensburg H, Tooze RP, Foster DF, Slawin AMZ (2004) Inorg Chem 43:2468–2470
van Rensburg H, Tooze RP, Foster DF, Otto S (2007) Inorg Chem 46:1963–1965
Llewellyn SA, Green MLH, Cowley AR (2006) Dalton Trans 4164–4168
EliBracht P, Barfacker L, Buss C, Hollmann C, Kitsos-Rzychon BE, Kranemann CL, Rische T, Roggenbuck R, Schmidt A (1999) Chem Rev 99:3329–3366
Ahmed M, Seayad AM, Jackstell R, Beller M (2003) J Am Chem Soc 125:10311–10318
Seayad AM, Selvakumar K, Ahmed M, Beller M (2003) Tetrahedron Lett 44:1679–1683
Ahmed M, Buch C, Routaboul L, Jackstell R, Klein H, Spannenberg A, Beller M (2007) Chem Eur J 13:1594–1601
Kollar L (2008) Modern carbonylation methods. Wiley-VCH, Weinheim
Calo V, Giannoccaro P, Nacci A, Monopoli A (2002) J Organomet Chem 645:152–157
Mizushima E, Hayashi T, Tanaka M (2001) Green Chem 3:76–79
Fukuyama T, Inouye T, Ryu I (2007) J Organomet Chem 692:685–690
Zawartka W, Trzeciak AM, Ziolkowski JJ, Lis T, Ciunik Z, Pernak J (2006) Adv Synth Cat 348:1689–1698
Zheng S, Xu L, Xia C (2007) Appl Organomet Chem 21:772–776
Liu J, Zhang R, Wang S, Sun W, Xia C (2009) Org Lett 6:1321–1324
Zheng S, Li F, Liu J, Xia C (2007) Tetrahedron Lett 48:5883–5886
Zheng S, Peng X, Liu J, Sun W, Xia C (2007) Helv Chim Acta 90:1471–1476
Zheng S, Peng X, Liu J, Sun W, Xia C (2007) Chin J Chem 25:1065–1068
Okuyama K, Sugiyama J, Nagahata R, Asai M, Ueda M, Takeuchi K (2003) J Mol Cat A: Chem 203:21–27
Okuyama K, Sugiyama J, Nagahata R, Asai M, Ueda M, Takeuchi K (2003) Macromolecules 36:6953–6955
Okuyama K, Sugiyama J, Nagahata R, Asai M, Ueda M, Takeuchi K (2003) Green Chem 5:563–566
Layman P (1996) C&EN July 1, pp 7–8
Gardiner MG, Herrmann WA, Reisinger CP, Schwarz J, Spiegler M (1999) J Organomet Chem 572:239–247
Drent E, Budzelaar PHM (1996) Chem Rev 96:663–681
Chen JCC, Lin IJB (2000) Organometallics 19:5113–5121
Andrus MB, Ma Y, Zang Y, Song C (2002) Tetrahedron Lett 43:9137–9140
Ma Y, Song C, Chai Q, Ma C, Andrus MB (2003) Synthesis 2886–2889
Doughty DH, Pignolet LH (1983) Homogenous catalysis with metal phosphine complexes. Plenum, New York, pp 343–375, Chapter 11
Crabtree RH (2005) The organometallic chemistry of the transition metals. Wiley, New Jersey
Matsudu T, Shigeno M, Murakami M (2006) Chem Lett 35:288–289
Gomes LFR, Trindade AF, Candeias NR, Gois PMP, Afonso CAM (2008) Tetrahedron Lett 49:7372–7375
Andrus MB, Liu J (2006) Tetrahedron Lett 47:5811–5814
Sparta M, Borve KJ, Jensen VR (2007) J Am Chem Soc 129:8487–8499
Halpern J (1982) Science 217:401–407
Chan ASC, Pluth JJ, Halpern J (1980) J Am Chem Soc 102:5952–5954
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Jeletic, M., Veige, A. (2010). N-Heterocyclic Carbene Complexes in Reactions Involving Carbon Monoxide. In: Cazin, C. (eds) N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis. Catalysis by Metal Complexes, vol 32. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-2866-2_9
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