Synthesis, structure, and catalytic activity of a new chiral NHC-iridium(III) complex

Inorganic Chemistry Communications

Volumn 29, Issue , 2013, Pages 141-144

  Chen, Liang ^a   Liu, Yuqiao ^a,b   Hou, Guohua ^a   Song, Haibin ^b   Zi, Guofu ^a  

^a BEIJING NORMAL UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

Asymmetric hydrosilylation; Biphenyl ligand; Carbene complex; Iridium

Indexed keywords

EID: 84874311015     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2012.12.026     Document Type: Article

References (46)

1. F.E. Hahn, and M.C. Jahnke Heterocyclic carbenes: synthesis and coordination chemistry Angew. Chem. Int. Ed. 47 2008 3122 3172
2. J.C.Y. Lin, R.T.W. Huang, C.S. Lee, A. Bhattacharyya, W.S. Hwang, and I.J.B. Lin Coinage metal-N-heterocyclic carbene complexes Chem. Rev. 109 2009 3561 3598
3. S. Díez-González, N. Marion, and S.P. Nolan N-Heterocyclic carbenes in late transition metal catalysis Chem. Rev. 109 2009 3612 3676
4. W. Gil, and A.M. Trzeciak N-Heterocyclic carbene-rhodium complexes as catalysts for hydroformylation and related reactions Coord. Chem. Rev. 255 2011 473 483
5. S.P. Nolan The development and catalytic uses of n-heterocyclic carbene gold complexes Acc. Chem. Res. 44 2011 91 100
6. M. Bierenstiel, and E.D. Cross Sulfur-functionalized N-heterocyclic carbenes and their transition metal complexes Coord. Chem. Rev. 255 2011 574 590
7. G.C. Fortman, and S.P. Nolan N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union Chem. Soc. Rev. 40 2011 5151 5169
8. J.A. Cabeza, and P. García-Álvarez The N-heterocyclic carbene chemistry of transition-metal carbonyl clusters Chem. Soc. Rev. 40 2011 5389 5405
9. S. Gaillard, C.S.J. Cazin, and P. Nolan N-Heterocyclic carbene gold(I) and copper(I) complexes in CH bond activation Acc. Chem. Res. 45 2012 778 787
10. C. Valente, S. Çalimsiz, K.H. Hoi, D. Mallik, M. Sayah, and M.G. Organ The development of bulky palladium NHC complexes for the most-challenging cross-coupling reactions Angew. Chem. Int. Ed. 51 2012 3314 3332
11. M.J. Ingleson, and R.A. Layfield N-Heterocyclic carbene chemistry of iron: fundamentals and applications Chem. Commun. 48 2012 3579 3589
12. S. Budagumpi, R.A. Haque, and A.W. Salman Stereochemical and structural characteristics of single- and double-site Pd(II)-N-heterocyclic carbene complexes: promising catalysts in organic syntheses ranging from CC coupling to olefin polymerizations Coord. Chem. Rev. 256 2012 1787 1830
13. M.C. Perry, and K. Burgess Chiral N-heterocyclic carbene-transition metal complexes in asymmetric catalysis Tetrahedron-Asymmetry 14 2003 951 961
14. V. César, S. Bellemin-Laponnaz, and L.H. Gade Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis Chem. Soc. Rev. 33 2004 619 636
15. S. Roland, and P. Mangeney Chiral diaminocarbene complexes, synthesis and application in asymmetric catalysis Top. Organomet. Chem. 15 2005 191 229
16. R.E. Douthwaite Metal-mediated asymmetric alkylation using chiral N-heterocyclic carbenes derived from chiral amines Coord. Chem. Rev. 251 2007 702 717
17. L.H. Gade, and S. Bellemin-Laponnaz Mixed oxazoline-carbenes as stereodirecting ligands for asymmetric catalysis Coord. Chem. Rev. 251 2007 718 725
18. D.R. Snead, H. Seo, and S. Hong Recent developments of chiral diaminocarbene-metal complexes for asymmetric catalysis Curr. Org. Chem. 12 2008 1370 1387
19. L.N. Gu, G.B. Zhu, H.B. Song, and G.F. Zi Progress in preparation of chiral NHC-metal complexes and their use as catalysts in asymmetric reactions Chin. J. Org. Chem. 29 2009 1499 1507
20. T.J. Seiders, D.W. Ward, and R.H. Grubbs Enantioselective ruthenium-catalyzed ring-closing metathesis Org. Lett. 3 2001 3225 3228
21. K. Lee, M.K. Brown, A.W. Hird, and A.H. Hoveyda A practical method for enantioselective synthesis of all-carbon quaternary stereogenic centers through NHC-Cu-catalyzed conjugate additions of alkyl- and arylzinc reagents to β-substituted cyclic enones J. Am. Chem. Soc. 128 2006 7182 7184
22. D. Martin, S. Kehrli, M. d'Augustin, H. Clavier, M. Mauduit, and A. Alexakis Copper-catalyzed asymmetric conjugate addition of grignard reagents to trisubstituted enones. Construction of all-carbon quaternary chiral centers J. Am. Chem. Soc. 128 2006 8416 8417
23. K.S. Lee, and A.H. Hoveyda Enantioselective conjugate silyl additions to cyclic and acyclic unsaturated carbonyls catalyzed by cu complexes of chiral N-heterocyclic carbenes J. Am. Chem. Soc. 132 2010 2898 2900
24. S. Lee, and J.F. Hartwig Improved catalysts for the palladium-catalyzed synthesis of oxindoles by amide α-arylation. Rate acceleration, use of aryl chloride substrates, and a new carbene ligand for asymmetric transformations J. Org. Chem. 66 2001 3402 3415
25. L.C. Bonnet, R.E. Douthwaite, and B.M. Kariuki Synthesis of new chiral N-heterocyclic carbene-imine ligands and their application to an asymmetric allylic alkylation reaction Organometallics 22 2003 4187 4189
26. A. Ros, D. Monge, M. Alcarazo, E. Álvarez, J.M. Lassaletta, and R. Fernández Synthesis, structure, and applications of N-dialkylamino- N′-alkylimidazol-2-ylidenes as a new type of NHC ligands Organometallics 25 2006 6039 6046
27. S.J. Roseblade, A. Ros, D. Monge, M. Alcarazo, E. Álvarez, J.M. Lassaletta, and R. Fernández Imidazo[1,5-a]pyridin-3-ylidene/thioether mixed C/S ligands and complexes thereof Organometallics 26 2007 2570 2578
28. M.C. Perry, X.H. Cui, M.T. Powell, D.R. Hou, J.H. Reibenspies, and K. Burgess Optically active iridium imidazol-2-ylidene-oxazoline complexes: preparation and use in asymmetric hydrogenation of arylalkenes J. Am. Chem. Soc. 125 2003 113 123
29. W.A. Herrmann, L.J. Goossen, C. Köcher, and G.R. Artus Chiral heterocylic carbenes in asymmetric homogeneous catalysis Angew. Chem. Int. Ed. 35 1996 2805 2807
30. J.W. Faller, and P.P. Fontaine Stereodynamics and asymmetric hydrosilylation with chiral rhodium complexes containing a monodentate N-heterocyclic carbene Organometallics 25 2006 5887 5893
31. W.-L. Duan, M. Shi, and G.-B. Rong Synthesis of novel axially chiral Rh-NHC complexes derived from BINAM and application in the enantioselective hydrosilylation of methyl ketones Chem. Commun. 2003 2916 2917
32. Q. Xu, X. Gu, S. Liu, Q. Dou, and M. Shi The use of chiral BINAM NHC-Rh(III) complexes in enantioselective hydrosilylation of 3-oxo-3-arylpropionic acid methyl or ethyl esters J. Org. Chem. 72 2007 2240 2242
33. L. Xiang, Q. Wang, H. Song, and G. Zi Synthesis, structural characterization, and reactivity of organolanthanides derived from a new chiral ligand, (R)-Bis(pyrrol-2-ylmethyleneamino)-1,1′-binaphthyl Organometallics 26 2007 5323 5329
34. G. Zi, L. Xiang, and H. Song Enantioselective hydroamination/cyclization catalyzed by organolanthanide amides derived from a new chiral ligand, (S)-2-(pyrrol-2-ylmethyleneamino)-2′-dimethylamino-1,1′-binaphthyl Organometallics 27 2008 1242 1246
35. Q. Wang, L. Xiang, H. Song, and G. Zi Synthesis of amidolanthanides with new chiral biaryl-based NNO ligands and their use as catalysts for enantioselective hydroamination/cyclization Inorg. Chem. 47 2008 4319 4328
36. G. Zi, Q. Wang, L. Xiang, and H. Song Lanthanide and group 4 metal complexes with new chiral biaryl-based NNO-donor ligands Dalton Trans. 2008 5930 5944
37. G. Zi, X. Liu, L. Xiang, and H. Song Synthesis of group 4 metal amides with new chiral biaryldiamine-based ligands and their use as catalysts for asymmetric hydroamination/cyclization Organometallics 28 2009 1127 1137
38. G. Zi Asymmetric hydroamination/cyclization catalyzed by organolanthanide complexes with chiral biaryl-based ligands Dalton Trans. 2009 9101 9109
39. 2-symmetric binaphthyldiamine-based ligands and their use as catalysts for asymmetric hydroamination/cyclization Dalton Trans. 39 2010 4048 4061
40. G. Zi, F. Zhang, and H. Song Highly enantioselective hydroaminoalkylation of secondary amines catalyzed by group 5 metal amides with chiral biarylamidate ligands Chem. Commun. 46 2010 6296 6298
41. G. Zi Asymmetric hydroamination/cyclization catalyzed by group 4 metal complexes with chiral biaryl-based ligands J. Organomet. Chem. 696 2011 68 75
42. F. Zhang, H. Song, and G. Zi Synthesis and catalytic activity of group 5 metal amides with chiral biaryldiamine-based ligands Dalton Trans. 40 2011 1547 1566
43. H. Song, L.N. Gu, and G. Zi Synthesis and X-ray structures of rhodium complexes with new chiral biaryl-based NHC-ligands J. Organomet. Chem. 694 2009 1493 1502
44. H. Song, Y. Liu, D. Fan, and G. Zi Synthesis, structure, and catalytic activity of rhodium complexes with new chiral binaphthyl-based NHC-ligands J. Organomet. Chem. 696 2011 3714 3720
45. M. Poyatos, M. Sanaú, and E. Peris New Rh(I) and Rh(III) bisimidazol-2-ylidene complexes: synthesis, reactivity, and molecular structures Inorg. Chem. 42 2003 2572 2576
46. A.R. Chianese, A. Mo, N.L. Lampland, R.L. Swartz, and P.T. Bremer Organometallics 29 2010 3019 3026