Aerobic alcohol oxidation coupled to palladium-catalyzed alkene hydroarylation with boronic esters

Angewandte Chemie - International Edition

Volumn 47, Issue 17, 2008, Pages 3219-3222

  Iwai, Yasumasa ^a   Gligorich, Keith M ^a   Sigman, Matthew S ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

Cross coupling; Homogeneous catalysis; Molecular oxygen; Palladium; Reaction mechanisms

Indexed keywords

CATALYSIS; ESTERS; MOLECULAR OXYGEN; OLEFINS; OXIDATION; PALLADIUM; REGIOSELECTIVITY; STYRENE;

AEROBIC ALCOHOL OXIDATIONS; CHEMICAL EQUATIONS; CROSS-COUPLINGS; FUNCTIONALIZATIONS; HOMOGENEOUS CATALYSIS; INITIAL OXIDATION; PALLADIUM-CATALYZED; REACTION MECHANISM;

PALLADIUM COMPOUNDS;

ALCOHOL DERIVATIVE; ALKENE; BORONIC ACID DERIVATIVE; OXYGEN; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY;

ALCOHOLS; ALKENES; BORONIC ACIDS; CATALYSIS; OXYGEN; PALLADIUM;

EID: 45549103074     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705317     Document Type: Article

References (36)

1. J. Tsuji, Palladium Reagents and Catalysts, Wiley, Hoboken, NJ, 2004, pp. 288-313.
2. a) S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633-9695;
3. b) K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516-4563;
4. Angew. Chem. Int. Ed. 2005, 44, 4442-4489.
5. N. Yasuda, J. Organomet. Chem. 2002, 653, 279-287.
6. a) S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4676-4701;
7. Angew. Chem. Int. Ed. 2001, 40, 4544-4568;
8. b) N. Miyaura, J. Organomet. Chem. 2002, 653, 54-57.
9. K. M. Gligorich, S. A. Cummings, M. S. Sigman, J. Am. Chem. Soc. 2007, 129, 14193-14195.
10. a) S. S. Stahl, Angew. Chem. 2004, 116, 3480-3501;
11. Angew. Chem. Int. Ed. 2004, 43, 3400-3420;
12. b) K. M. Gligorich, M. S. Sigman, Angew. Chem. 2006, 118, 6764-6767;
13. Angew. Chem. Int. Ed. 2006, 45, 6612-6615.
14. M. S. Sigman, D. R. Jensen, Acc. Chem. Res. 2006, 39, 221-229.
15. I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 13178-13179.
16. For a Rh-catalyzed hydroarylation reaction of vinyl pyridine with an arylboronic acid, see: a) M. Lautens , A. Roy, K. Fukuoka, K. Fagnou, B. Martin-Matute, J. Am. Chem. Soc. 2001, 123, 5358-5359.
17. For examples of Pd-catalyzed hydroarylations of Michael acceptors with organoboranes, see: b) T. Nishikata, Y. Yamamoto, N. Miyaura, Organometallics 2004, 23, 4317-4324;
18. c) S. C. Pellegrinet, J. M. Goodman, J. Am. Chem. Soc. 2006, 128, 3116-3117.
19. a) For an example of an oxidative Heck reaction with an arylboronic acid, see: M. M. S. Andappan, P. Nilsson, H. Von Schenck, M. Larhed, J. Org. Chem. 2004, 69, 5212-5218;
20. b) For a recent mechanistic study of the oxidative Heck reaction, see: P.-A. Enquist, P. Nilsson, P. Sjoberg , M. Larhed, J. Org. Chem. 2006, 71, 8779-8786.
21. D. R. Jensen, M. J. Schultz, J. A. Mueller, M. S. Sigman, Angew. Chem. 2003, 115, 3940-3943;
22. Angew. Chem. Int. Ed. 2003, 42, 3810-3813.
23. a) M. S. Viciu, S. P. Nolan in Topics in Organometallic Chemistry, Vol. 14, Springer, Berlin, 2005, pp.241-278;
24. b) N. M. Scott, S. P. Nolan in N-Heterocyclic Carbenes in Synthesis (Ed.: S. P. Nolan), Wiley-VCH, Weinheim, 2006, pp. 55-72;
25. c) E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Angew. Chem. 2007, 119, 2824-2870;
26. Angew. Chem. Int. Ed. 2007, 46, 2768-2813.
27. J. Kischel, I. Jovel, K. Mertins, A. Zapf, M. Beller, Org. Lett. 2006, 8, 19-22.
28. Acid sensitive functional groups are not compatible with previously reported Lewis acid catalyzed hydroarylation reactions of alkenes. For an example, see: M. Rueping, B. J. Nachtsheim, T. Scheidt, Org. Lett. 2006, 8, 3717-3719.
29. A. M. Johns, M. Utsunomiya, C. D. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 1828-1839.
30. See the Supporting Information for details.
31. For examples of Pd-catalyzed oxidative homocoupling of boronic acids, see: a) D. J. Koza, E. Carita, Synthesis 2002, 2183-2186;
32. b) H. Yoshida, Y. Yamaryo, J. Ohshita, A. Kunai, Tetrahedron Lett. 2003, 44, 1541-1544;
33. c) C. Adamo, C. Amatore, I. Ciofini, A. Jutand, H. Lakmini, J. Am. Chem. Soc. 2006, 128, 6829-6836.
34. a) C. Adamo, C. Amatore, I. Ciofini, A. Jutand, H. Lakmini, J. Am. Chem. Soc. 2006, 128, 6829-6836;
35. b) K. S. Yoo, C. P. Park, C. H. Yoon, S. Sakaguchi, J. O'Neill, K. W. Jung, Org. Lett. 2007, 9, 3933-3935.
36. C. J. O'Brien, E. A. B. Kantchev, C. Valente, N. Hadei, G. A. Chass, A. Lough, A. C. Hopkinson, M. G. Organ, Chem. Eur. J. 2006, 12, 4743-4748.