Selective arylation of aldehydes with di-rhodium(II)/NHC catalysts

Tetrahedron

Volumn 66, Issue 44, 2010, Pages 8494-8502

  Trindade, Alexandre F ^a   André, Vânia ^a   Duarte, M Teresa ^a   Veiros, Luís F ^a   Gois, Pedro M P ^b   Afonso, Carlos A M ^a,b  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^b RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

Author keywords

Alcohol racemization; Arylation; Boronic acids; Catalysis; DFT calculations; N Heterocycliccarbenes (NHC); Rhodium (II)

Indexed keywords

ALDEHYDE DERIVATIVE; BORONIC ACID DERIVATIVE; CARBENE; HETEROCYCLIC COMPOUND; RHODIUM COMPLEX; VINYL DERIVATIVE;

ARTICLE; ARYLATION; CALCULATION; CATALYST; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; ELECTRON; PRIORITY JOURNAL; RACEMIZATION;

EID: 77957754008     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.08.050     Document Type: Article

References (57)

1. K. Fagnou, and M. Lautens Chem. Rev. 103 2003 169
2. C. Bolm, J.P. Hildebrand, K. Muñiz, and N. Hermanns Angew. Chem., Int. Ed. 40 2001 3284
3. F. Schmidt, R.T. Stemmler, J. Rudolph, and C. Bolm Chem. Soc. Rev. 35 2006 454
4. R. Lerebours, and C. Wolf J. Am. Chem. Soc. 128 2006 13052
5. Y. Muramatsu, and T. Harada Chem. - Eur. J. 14 2008 10560
6. Y.-X. Liao, C.-H. Xing, P. He, and Q.-S. Hu Org. Lett. 10 2008 2509
7. Y. Yamamoto, K. Kurihara, and N. Miyaura Angew. Chem., Int. Ed. 48 2009 4414
8. T. Zou, S.-S. Pi, and J.-H. Li Org. Lett. 11 2009 453
9. H. Zheng, Q. Zhang, J. Chen, M. Liu, S. Cheng, J. Ding, H. Wu, and W. Su J. Org. Chem. 74 2009 943
10. T. Arao, K. Kondo, and T. Aoyama Tetrahedron Lett. 48 2007 4115
11. K. Biswas, O. Prieto, P.J. Goldsmith, and S. Woodward Angew. Chem., Int. Ed. 44 2005 2232
12. A. Fürstner, and H. Krause Adv. Synth. Catal. 343 2001 343
13. C. Bolm, and K. Muñiz Chem. Commun. 1999 1295
14. C. Bolm, N. Hermanns, J.P. Hildebrand, and K. Muñiz Angew. Chem., Int. Ed. 39 2000 3465
15. P.M.P. Góis, A.F. Trindade, L.F. Veiros, V. André, M.T. Duarte, C.A.M. Afonso, S. Caddick, and F.G.N. Cloke Angew. Chem., Int. Ed. 46 2007 5750
16. A.F. Trindade, P.M.P. Góis, L.F. Veiros, V. André, M.T. Duarte, C.A.M. Afonso, S. Caddick, and F.G.N. Cloke J. Org. Chem. 73 2008 4076
17. P. Zhao, C.D. Incarvito, and F. Hartwig J. Am. Chem. Soc. 129 2007 1876
18. L. Farrugia J. Appl. Crystallogr. 30 1997 565
19. K.B. Wiberg Tetrahedron 24 1968 1083 Wiberg indices are electronic parameters related to the electron density between atoms. They can be obtained from a Natural Population Analysis and provide an indication of the bond strength.
20. J.E. Carpenter, and F.J. Weinhold Mol. Struct. (Theochem) 169 1988 41
21. Carpenter, J.E. PhD Thesis, University of Wisconsin Madison WI, 1987;
22. J.P. Foster, and F. Weinhold J. Am. Chem. Soc. 102 1980 7211
23. A.E. Reed, and F.J. Weinhold Chem. Phys. 78 1983 4066
24. A.E. Reed, and F.J. Weinhold Chem. Phys. 78 1983 1736
25. A.E. Reed, R.B. Weinstock, and F.J. Weinhold Chem. Phys. 83 1985 735
26. A.E. Reed, L.A. Curtiss, and F. Weinhold Chem. Rev. 88 1988 899
27. F. Weinhold, and J.E. Carpenter The Structure of Small Molecules and Ions 1988 Plenum New York, NY p 227
28. J. Lloret, J.J. Carbó, C. Bo, A. Lledós, and J. Pérez-Prieto Organometallics 27 2008 2873
29. For examples of enantioselective rhodium catalyzed aldehydes arylations reactions see:
30. H.F. Duan, J.H. Xie, W.J. Shi, Q. Zhang, and Q.L. Zhou Org. Lett. 8 2006 1479
31. R.B.C. Jagt, P.Y. Toullec, J.G. de Vries, B.L. Feringa, and A.J. Minnaard Org. Biomol. Chem. 4 2006 773
32. S.L.X. Martina, R.B.C. Jagt, J.G. de Vries, B.L. Feringa, and A.J. Minnaard Chem. Commun. 2006 4093
33. T. Nishimura, H. Kumamoto, M. Nagaosa, and T. Hayashi Chem. Commun. 2009 5713
34. T. Noel, K. Vandyck, and J. Van der Eycken Tetrahedron 63 2007 12961
35. H.M.L. Davies, and R.E.J. Beckwith Chem. Rev. 103 2003 2861
36. P.M.P. Góis, and C.A.M. Afonso Eur. J. Org. Chem. 2004 3773
37. P.M. Dinh, J.A. Howarth, A.R. Hudnott, J.M.J. Williams, and W. Harris Tetrahedron Lett. 37 1996 7623
38. A.J. Arduengo III, R. Krafczyk, R. Schmutzer, H.A. Craig, J.R. Goerlich, W.J. Marshall, and M. Unverzagt Tetrahedron 55 1999 14523
39. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, and J.A. Pople Gaussian 98, Revision A.7 1998 Gaussian, Pittsburgh, PA and provide an indication of the bond strength
40. W.J. Hehre, L. Radom, P.v.R. Schleyer, and J.A. Pople Ab Initio Molecular Orbital Theory 1986 John Wiley & Sons New York, NY
41. R.G. Parr, and W. Yang Density Functional Theory of Atoms and Molecules 1989 Oxford University New York, NY
42. A.D.J. Becke Chem. Phys. 98 1993 5648
43. K. Burke, J.P. Perdew, and Y. Wang J.F. Dobson, G. Vignale, M.P. Das, Electronic Density Functional Theory: Recent Progress and New Directions 1998 Plenum New York, NY
44. J.P. Perdew P. Ziesche, H. Eschrig, Electronic Structure of Solids '91 1991 Akademie Berlin 11
45. J.P. Perdew, J.A. Chevary, S.H. Vosko, K.A. Jackson, M.R. Pederson, D.J. Singh, and C. Fiolhais Phys. Rev. B 46 1992 6671
46. J.P. Perdew, J.A. Chevary, S.H. Vosko, K.A. Jackson, M.R. Pederson, D.J. Singh, and C. Fiolhais Phys. Rev. B 48 1993 4978
47. J.P. Perdew, K. Burke, and Y. Wang Phys. Rev. B 54 1996 16533
48. T.H. Dunning Jr., and P.J. Hay H.F. Schaefer III Modern Theoretical Chemistry Vol. 3 1976 Plenum New York, NY 1
49. P.J. Hay, and W.R. Wadt J. Chem. Phys. 82 1985 270
50. W.R. Wadt, and P.J. Hay J. Chem. Phys. 82 1985 284
51. P.J. Hay, and W.R. Wadt J. Chem. Phys. 82 1985 2299
52. A.W. Ehlers, M. Böhme, S. Dapprich, A. Gobbi, A. Höllwarth, V. Jonas, K.F. Köhler, R. Stegmann, A. Veldkamp, and G. Frenking Chem. Phys. Lett. 208 1993 111
53. R. Ditchfield, W.J. Hehre, and J.A. Pople J. Chem. Phys. 54 1971 724
54. W.J. Hehre, R. Ditchfield, and J.A. Pople J. Chem. Phys. 56 1972 2257
55. P.C. Hariharan, and J.A. Pople Mol. Phys. 27 1974 209
56. M.S. Gordon Chem. Phys. Lett. 76 1980 163
57. P.C. Hariharan, and J.A. Pople Theor. Chim. Acta 28 1973 213