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Synlett 2011(12): 1649-1653
DOI: 10.1055/s-0030-1260799
DOI: 10.1055/s-0030-1260799
SYNPACTS
© Georg Thieme Verlag
Stuttgart ˙ New YorkNHC-NiH Reactions with Simple Olefins: Advances in Hydroalkenylation, Polymerization, and Ionic-Liquid Synthesis
Further Information
Received
28 December 2010
Publication Date:
21 June 2011 (online)
Publication History
Publication Date:
21 June 2011 (online)

Abstract
Various NHC-NiH species have been developed as hydroalkenylation and polymerization catalysts and for ionic-liquid synthesis. This article outlines their key features and connections and highlights the opportunities for using NHC-NiH species in the selective preparation of new geminal disubstituted olefins and how they complement traditional P-NiH technology.
Key words
N-heterocyclic carbene - homogeneous Ni catalysis - geminal disubstituted alkene - regioselective insertion - co-dimer
- 1
Alpha
Olefins Applications Handbook
Lappin GR.Sauer JD. Marcel Dekker; New York: 1989. - 2a
Handbook of Transition Metal Polymerization
Catalysts
Hoff R.Mathers RT. J. Wiley and Sons; Hoboken: 2010. - 2b
Camacho DH.Guan Z. Chem. Commun. 2010, 46: 7879 - 2c
McGuinness DS. Chem. Rev. 2011, 111: 2321 - 3a
Jolly PW.Wilke G. In Applied Homogeneous Catalysis with Organometallic Compounds Vol. 3:Cornils B.Hermann WA. Wiley-VCH; Weinheim: 2002. p.1164 - 3b
Grabulosa A.Muller G.Ordinas JI.Mezzetti A.Maestro MA.Font-Bardia M.Solans X. Organometallics 2005, 24: 4961 - 3c
RajanBabu TV. Synlett 2009, 853 - 3d
Vogt D. Angew. Chem. Int. Ed. 2010, 49: 7166 - Recent advance in asymmetric hydrovinylation:
- 4a
Grutters MMP.Mueller C.Vogt D. J. Am. Chem. Soc. 2006, 128: 7414 - 4b
Zhang A.RajanBabu TV.
J. Am. Chem. Soc. 2006, 128: 5620 - 4c
Smith CR.RajanBabu TV. Org. Lett. 2008, 10: 1657 - 4d
Lassauque N.Francio G.Leitner W. Adv. Synth. Catal. 2009, 351: 3133 - 4e
Lassauque N.Francio G.Leitner W. Eur. J. Org. Chem. 2009, 3199 - 4f
Sharma RK.RajanBabu TV. J. Am. Chem. Soc. 2010, 132: 3295 - 4g
Liu W.RajanBabu TV. J. Org. Chem. 2010, 75: 7636 - 5a
Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1290 - 5b
Louie J. In N-Heterocyclic Carbenes in SynthesisNolan SP. Wiley-VCH; Weinheim: 2006. p.163 - 5c
Tekavec TN.Louie J. In N-Heterocyclic Carbenes in Transition Metal CatalysisGlorius F. Springer; Berlin: 2006. p.159 - 5d
McGuinness DS.Cavell KJ. In N-Heterocyclic Carbenes in Transition Metal Catalysis and OrganocatalysisCazin CSJ. Springer; New York: 2011. p.105 - 6a
Clement ND.Cavell KJ. Angew. Chem. Int. Ed. 2004, 43: 3845 - 6b
Cavell KJ.McGuinness DS. Coord. Chem. Rev. 2004, 248: 671 - For unusual trans reductive elimination, see:
- 6c
Steineke T.Shaw BK.Jong H.Patrick BO.Fryzuk MD.Green JC. J. Am. Chem. Soc. 2009, 131: 10461 - 7a
Normand AT.Hawkes KJ.Clement ND.Cavell KJ.Yates BF. Organometallics 2007, 26: 5352 - 7b
McGuinness DS.Cavell KJ.Skelton BW.White AH. Organometallics 1999, 18: 1596 - 8a
Lee S.-G. Chem. Commun. 2006, 1049 - 8b
Canal JP.Ramnial T.Dickie DA.Clyburne JAC. Chem. Commun. 2006, 1809 - 9
MacKinnon AL.Baird MC. J. Organomet. Chem. 2003, 683: 114 - 10a
Wang X.Liu S.Jin G.-X. Organometallics 2004, 23: 6002 - 10b
Ketz BE.Ottenwaelder XG.Waymouth RM. Chem. Commun. 2005, 5693 - 10c
Ma R.Hou Y.Gao J.Bao F. Polym. Rev. 2009, 49: 249 - 10d
Berding J.Lutz M.Spek AL.Bouwman E. Appl. Organometal. Chem. 2011, 25: 76 - 11
Klabunde U.Mulhaupt R.Herskovitz T.Janowicz AH.Calabrese J.Ittel SD. J. Polym. Sci., Part A: Polym. Chem. 1987, 25: 1989 - 12a
Chauvin Y.Einloft S.Olivier H. Ind. Eng. Chem. Res. 1995, 34: 1149 - 12b
Ellis B.Keim W.Wasserscheid P. Chem. Commun. 1999, 337 - 13
McGuinness DS.Mueller W.Wasserscheid P.Cavell KJ.Skelton BW.White AH.Englert U. Organometallics 2002, 21: 175 - 14a
Dible BR.Sigman MS. J. Am. Chem. Soc. 2003, 125: 872 - 14b
Dible BR.Sigman MS. Inorg. Chem. 2006, 45: 8430 - 15
Clavier H.Nolan SP. Chem. Commun. 2010, 46: 841 - 16
Tekavec TN.Louie J. Tetrahedron 2008, 64: 6870 - Diene:
- 17a
Sato Y.Sawaki R.Mori M. Organometallics 2001, 20: 5510 - Alkyne:
- 17b
Knapp-Reed B.Mahandru GM.Montgomery J. J. Am. Chem. Soc. 2005, 127: 13156 - 17c
Malik HA.Sormunen GJ.Montgomery J. J. Am. Chem. Soc. 2010, 132: 6304 - Alkene:
- 17d
Ho C.-Y.Jamison TF. Angew. Chem. Int. Ed. 2007, 46: 782 - 18
Lim HJ.Smith CR.RajanBabu TV. J. Org. Chem. 2009, 74: 4565 - 19
Ho C.-Y. Chem. Commun. 2010, 46: 466 - 20
Ho C.-Y.He L. Angew. Chem. Int. Ed. 2010, 49: 9182 - 21
Nandi M.Jin J.RajanBabu TV. J. Am. Chem. Soc. 1999, 121: 9899 - 22
Joseph J.RajanBabu TV.Jemmis ED. Organometallics 2009, 28: 3552 - Allylic substitution:
- 23a
Matsubara R.Jamison TF. J. Am. Chem. Soc. 2010, 132: 6880 - α-Selective hydrometallation of alkynes:
- 23b
Gao F.McGrath KP.Lee Y.Hoveyda AH. J. Am. Chem. Soc. 2010. 132, p.14315 - Enone-allene reductive coupling:
- 23c
Li W.Chen N.Montgomery J. Angew. Chem. Int. Ed. 2010, 49: 8712 - 24
Broene RD.Brookhart M.Lamanna WM.Volpe AF. J. Am. Chem. Soc. 2005, 127: 17194 - 25a
Hilt G.DuMesnil F.-X.Luers S. Angew. Chem. Int. Ed. 2001, 40: 387 - 25b
Sanchez RP.Connell BT. Organometallics 2008, 27: 2902 - 25c
Hilt G.Treutwein J. Chem. Commun. 2009, 1395 - 25d
Hilt G.Danz M.Treutwein J. Org. Lett. 2009, 11: 3322 - 25e
Moreau B.Wu JY.Ritter T. Org. Lett. 2009, 11: 337 - 25f
Arndt M.Reinhold A.Hilt G. J. Org. Chem. 2010, 75: 5203 - 25g
Jeganmohan M.Cheng CH. Chem. Eur. J. 2008, 14: 10876 - 26
Ho C.-Y.Ohmiya H.Jamison TF. Angew. Chem., Int. Ed. 2008, 47: 1893