Palladium-catalyzed carbonylative coupling reactions of aryl iodides with hexamethyldisilane (HMDS) to benzoyl silanes

Tetrahedron Letters

Volumn 53, Issue 5, 2012, Pages 582-584

  Wu, Xiao Feng ^a,b   Neumann, Helfried ^b   Beller, Matthias ^b  

^a ZHEJIANG SCI TECH UNIVERSITY   (China)

^b LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

Acyl silane; Aryl iodides; Carbonylation; HMDS; Palladium

Indexed keywords

ARYL IODIDE DERIVATIVE; HEXAMETHYLDISILANE; IODINE DERIVATIVE; PALLADIUM; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL REACTION; SYNTHESIS;

EID: 84355162324     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.11.104     Document Type: Article

References (55)

1. A.G. Brook, and R.J. Mauris J. Am. Chem. Soc. 79 1957 971 973
2. A. Ricci, and A. Degl'Innocenti Synthesis 1989 647 660
3. P.C.B. Page, S.S. Klair, and S. Rosenthal Chem. Soc. Rev. 19 1990 147 195
4. P.F. Cirillo, and J.S. Panek Org. Prep. Proced. Int. 24 1992 555 582
5. C. Najera, and M. Yus Org. Prep. Proced. Int. 27 1995 385 456
6. B.F. Bonini, M. Comes-Franchini, M. Fochi, G. Mazzanti, and A. Ricci Gazz. Chim. Ital. 127 1997 619 628
7. B.F. Bonini, M. Comes-Franchini, M. Fochi, G. Mazzanti, and A. Ricci J. Organomet. Chem. 567 1998 181 189
8. P.C.B. Page, M.J. McKenzie, S.S. Klair, and S. Rosenthal S. Patai, Z. Rappoport, The Chemistry of Organosilicon Compounds Vol. 2 1998 Wiley Chichester, UK 1599 Part 2
9. For selected synthetic applications of acyl silanes, see: A. Degl'Innocenti, S. Pike, and D.R.M.J.C.S. Walton Chem. Commun. 1980 1201 1202
10. P.C.B. Page, S. Rosenthal, and R.V. Williams Tetrahedron Lett. 28 1987 4455 4456
11. J.C. Tarr, and J.S. Johnson Org. Lett. 11 2009 3870 3873
12. A.E. Mattson, and K.A. Scheidt Org. Lett. 6 2004 4363 4366
13. X. Lianghu, D.A. Nicewicz, and J.S. Johnson Org. Lett. 4 2002 2957 2960
14. R.F. Cunico, and B.C. Maity Org. Lett. 5 2003 4947 4949
15. S.-Y. Chang, W.-T. Jiaang, C.-D. Cherng, K.-H. Tang, C.-H. Huang, and Y.-M. Tsai J. Org. Chem. 62 1997 9089 9098
16. Y. Obora, M. Nakanishi, M. Tokunaga, and Y. Tsuji J. Org. Chem. 67 2002 5835 5837
17. J.C. Tarr, and J.S. Johnson J. Org. Chem. 75 2010 3317 3325
18. A.E. Mattson, A.R. Bharadwaj, A.M. Zuhl, and K.A. Scheidt J. Org. Chem. 71 2006 5715 5724
19. R.F. Cunico, and R.K. Pandey J. Org. Chem. 70 2005 5344 5346
20. R.B. Lettan II, C.V. Galliford, C.C. Woodward, and K.A. Scheidt J. Am. Chem. Soc. 131 2009 8805 8814
21. R.B. LettanII, T.E. Reynolds, C.V. Galliford, and K.A. Scheidt J. Am. Chem. Soc. 128 2006 15566 15567
22. Y. Obora, Y. Ogawa, Y. Imai, T. Kawamura, and Y. Tsuji J. Am. Chem. Soc. 123 2001 10489 10493
23. C.V. Galliford, and K.A. Scheidt Chem. Commun. 2008 1926 1928
24. R.B. Lettan II, C.C. Woodward, and K.A. Scheidt Angew. Chem., Int. Ed. 47 2008 2294 2297
25. K. Yamamoto, A. Hayashi, S. Suzuki, and J. Tsuji Organometallics 6 1987 974 979
26. J. Kang, J.H. Lee, K.S. Kim, J.U. Jeong, and C. Pyun Tetrahedron Lett. 28 1987 3216 3262
27. A.R. Katritzky, Z. Wang, and H. Lang Organometallics 15 1996 486 490
28. K. Suda, J.-I. Watanabe, and T. Takanami Tetrahedron Lett. 33 1992 1355 1356
29. A. Capperucci, A. Degl'Innocenti, C. Faggi, and A. Ricci J. Org. Chem. 53 1988 3612 3614
30. R.J. Linderman, and Y. Suhr J. Org. Chem. 53 1988 1569 1572
31. D. Seyferth, R.C. Hui, and W.-L. Wang J. Org. Chem. 58 1993 5843 5845
32. D. Seyferth, and R.M. Weinstein J. Am. Chem. Soc. 104 1982 5534 5535
33. F. Geng, and R.E. Maleczka Jr. Tetrahedron Lett. 40 1999 3113 3114
34. X.-F. Wu, H. Neumann, and M. Beller ChemCatChem 2 2010 509 513
35. X.-F. Wu, H. Neumann, and M. Beller Chem. Eur. J. 16 2010 9750 9753
36. X.-F. Wu, H. Neumann, and M. Beller Chem. Asian J. 5 2010 2168 2172
37. X.-F. Wu, H. Neumann, and M. Beller Angew. Chem., Int. Ed. 49 2010 5284 5288
38. X.-F. Wu, P. Anbarasan, H. Neumann, and M. Beller Angew. Chem., Int. Ed. 49 2010 7316 7319
39. X.-F. Wu, H. Neumann, and M. Beller Chem. Eur. J. 16 2010 12104 12107
40. X.-F. Wu, H. Neumann, and M. Beller Tetrahedron Lett. 51 2010 6146 6149
41. X.-F. Wu, H. Neumann, A. Spannenberg, T. Schulz, H. Jiao, and M. Beller J. Am. Chem. Soc. 132 2010 14596 14602
42. X.-F. Wu, B. Sundararaju, H. Neumann, P.H. Dixneuf, and M. Beller Chem. Eur. J. 17 2011 106 110
43. X.-F. Wu, H. Neumann, and M. Beller Adv. Synth. Catal. 353 2011 788 792
44. X.-F. Wu, H. Jiao, H. Neumann, and M. Beller ChemCatChem 3 2011 726 733
45. X.-F. Wu, B. Sundararaju, P. Anbarasan, H. Neumann, P.H. Dixneuf, and M. Beller Chem. Eur. J. 17 2011 8014 8017
46. X.-F. Wu, J. Schranck, H. Neumann, and M. Beller Chem. Eur. J. 17 2011 12246 12249
47. For reviews on palladium-catalyzed carbonylations, see: R. Grigg, and S.P. Mutton Tetrahedron 66 2010 5515 5548
48. A. Brennführer, H. Neumann, and M. Beller Angew. Chem., Int. Ed. 48 2009 4114 4133
49. A. Brennführer, H. Neumann, and M. Beller ChemCatChem 1 2009 28 41
50. R. Skoda-Földes, and L. Kollár Curr. Org. Chem. 6 2002 1097 1119
51. M. Beller, B. Cornils, C.D. Frohning, and C.W. Kohlpaintner J. Mol. Catal. A: Chem. 104 1995 17 85
52. X.-F. Wu, H. Neumann, and M. Beller Chem. Soc. Rev. 40 2011 4986 5009
53. 3 as ligand, see: K. Okura, S. Matsuoka, R. Goto, and M. Inoue Angew. Chem., Int. Ed. 49 2010 329 332
54. I. Paterson, A.D. Findlay, and C. Noti Chem. Commun. 2008 6408 6410
55. A.B. Smith III, T.M. Razler, G.R. Pettit, and J.-C. Chapuis Org. Lett. 7 2005 4403 4406