Allylic C-H alkylation of unactivated α-olefins: Serial ligand catalysis resumed

Angewandte Chemie - International Edition

Volumn 50, Issue 30, 2011, Pages 6824-6827

  Young, Andrew J ^a   White, M Christina ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

allylic alkylation; C H activation; ligand effects; palladium catalysis; sulfoxide ligands

Indexed keywords

ALLYLIC ALKYLATION; C-H ACTIVATION; LIGAND EFFECTS; PALLADIUM CATALYSIS; SULFOXIDE LIGANDS;

ACTIVATION ANALYSIS; ALKYLATION; CATALYSIS; OLEFINS;

LIGANDS;

EID: 79960275565     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201101654     Document Type: Article

References (51)

1. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921
2. J. Tsuji, in Palladium Reagents and Catalysts: New Perspectives for the 21st Century, 2 nd ed., Wiley, New York, 2005, pp. 431-517
3. G. Helmchen, A. Pfaltz, Acc. Chem. Res. 2000, 33, 336
4. J. T. Mohr, B. M. Stoltz, Chem. Asian J. 2007, 2, 1476
5. I species, see
6. G. Helmchen, A. Dahnz, P. Dübon, M. Schelwies, R. Weihofen, Chem. Commun. 2007, 675
7. P. A. Evans, D. K. Leahy, J. Am. Chem. Soc. 2003, 125, 8974.
8. A. J. Young, M. C. White, J. Am. Chem. Soc. 2008, 130, 14090
9. S. Lin, C.-X. Song, G.-X. Cai, W.-H. Wang, Z.-J. Shi, J. Am. Chem. Soc. 2008, 130, 12901; for a Cu/Co/TBHP (TBHP=tert-butyl hydroperoxide) system proceeding via radical intermediates, see
10. Z. Li, C.-J. Li, J. Am. Chem. Soc. 2006, 128, 56; for Ru- and Rh-catalyzed cycloisomerizations initiated by allylic C-H cleavage, see
11. B. M. Trost, F. D. Toste, J. Am. Chem. Soc. 1999, 121, 9728
12. Q. Li, Z.-X. Yu, J. Am. Chem. Soc. 2010, 132, 4542; for a unique example under reducing conditions, see
13. L. S. Hegedus, T. Hayashi, W. H. Darlington, J. Am. Chem. Soc. 1978, 100, 7747; for an early discussion of allylic C-H alkylation, see
14. B. M. Trost, L. Weber, P. E. Strege, T. J. Fullerton, T. J. Dietsche, J. Am. Chem. Soc. 1978, 100, 3416.
15. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
16. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
17. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976
18. Angew. Chem. Int. Ed. 2009, 48, 9792
19. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
20. Angew. Chem. Int. Ed. 2009, 48, 5094
21. M. Catellani, E. Motti, N. Della Ca', Acc. Chem. Res. 2008, 41, 1512
22. F. Kakiuchi, T. Kochi, Synthesis 2008, 3013
23. H. M. L. Davies, J. R. Manning, Nature 2008, 451, 417
24. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174
25. O. Daugulis, V. G. Zaitsev, D. Shabashov, Q.-N. Pham, A. Lazareva, Synlett 2006, 3382
26. L.-C. Campeau, K. Fagnou, Chem. Commun. 2006, 1253.
27. Intermolecular C-H esterifications of unactivated α-olefins with catalyst 2:, M. S. Chen, M. C. White, J. Am. Chem. Soc. 2004, 126, 1346.
28. J. H. Delcamp, M. C. White, J. Am. Chem. Soc. 2006, 128, 15076
29. D. J. Covell, M. C. White, Angew. Chem. 2008, 120, 6548
30. Angew. Chem. Int. Ed. 2008, 47, 6448; intermolecular C-H aminations of unactivated α-olefins with catalyst 1
31. S. A. Reed, M. C. White, J. Am. Chem. Soc. 2008, 130, 3316
32. S. A. Reed, A. R. Mazzotti, M. C. White, J. Am. Chem. Soc. 2009, 131, 11701.
33. K. J. Fraunhoffer, N. Prabagaran, L. E. Sirois, M. C. White, J. Am. Chem. Soc. 2006, 128, 9032
34. E. M. Stang, M. C. White, Nat. Chem. 2009, 1, 547; intramolecular allylic C-H aminations with catalyst 1
35. K. J. Fraunhoffer, M. C. White, J. Am. Chem. Soc. 2007, 129, 7274
36. G. T. Rice, M. C. White, J. Am. Chem. Soc. 2009, 131, 11707.
37. M. S. Chen, N. Prabagaran, N. A. Labenz, M. C. White, J. Am. Chem. Soc. 2005, 127, 6970.
38. X. Qi, G. T. Rice, M. S. Lall, M. S. Plummer, M. C. White, Tetrahedron 2010, 66, 4816
39. R. I. McDonald, S. S. Stahl, Angew. Chem. 2010, 122, 5661
40. Angew. Chem. Int. Ed. 2010, 49, 5529
41. B. P. Fors, S. L. Buchwald, J. Am. Chem. Soc. 2010, 132, 15914.
42. a value of allylbenzene has been reported as 34, see, K. Bowden, R. S. Cook, J. Chem. Soc. Perkin Trans. 2 1972, 1407.
43. B. A. Steinhoff, S. S. Stahl, J. Am. Chem. Soc. 2006, 128, 4348
44. B. A. Steinhoff, S. R. Fix, S. S. Stahl, J. Am. Chem. Soc. 2002, 124, 766.
45. R. Pathak, et al., Bioorg. Med. Chem. 2002, 10, 1695; for a synthesis of the Tsuji-Trost allylic carboxylate substrate for access to Table 2, entry 8, see
46. J. Uenishi, Y. S. Vikhe, Heterocycles 2010, 80, 1463.
47. S. E. Denmark, J. Fu, Chem. Rev. 2003, 103, 2763
48. S. R. Chemler, W. R. Roush, in Modern Carbonyl Chemistry (Ed.:, J. Otera,), Wiley-VCH, Weinheim, 2000, pp. 403-490
49. R. W. Hoffmann, in Asymmetric Synthesis (Eds.:, M. Christmann, S. Bräse,), Wiley-VCH, Weinheim, 2008, pp. 29-33.
50. R. Ballini, G. Bosica, D. Fiorini, A. Palmieri, Tetrahedron 2005, 61, 8971.
51. N. Ono, H. Miyake, R. Tamura, A. Kaji, Tetrahedron Lett. 1981, 22, 1705.