Palladium-catalyzed reductive coupling of styrenes and organostannanes under aerobic conditions

Journal of the American Chemical Society

Volumn 129, Issue 46, 2007, Pages 14193-14195

  Gligorich, Keith M ^a   Cummings, Sarah A ^a   Sigman, Matthew S ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKENE DERIVATIVE; CARBON; COPPER CHLORIDE; MANGANESE OXIDE; ORGANOTIN COMPOUND; PALLADIUM; SOLVENT; SPARTEINE; STYRENE DERIVATIVE;

AEROBIC CAPACITY; ARTICLE; ATOM; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; DECOMPOSITION; HECK REACTION; OXIDATION; REDUCTION;

AEROBIOSIS; CATALYSIS; MODELS, CHEMICAL; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PALLADIUM; STYRENES; TIN COMPOUNDS;

EID: 36448968256     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja076746f     Document Type: Article

References (33)

1. Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons Inc.: Hoboken, NJ, 2004; pp 27-29, 288-351.
2. Schlueter, A. D.; Bo, Z. Synthesis of Conjugated Polymers for Materials Science. In Handbook of Organopalladium Chemistry for Organic-Synthesis; John Wiley & Sons, Inc.; Hoboken, NJ, 2002; Vol. 1, pp 825-861.
3. King, A. O.; Yasuda, N. Top. Organomet. Chem. 2004, 6, 205-245.
4. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442-4489.
5. (a) Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221-229.
6. (b) Gligorich, K. M.; Schultz, M. J.; Sigman, M. S. J. Am. Chem. Soc. 2006, 128, 2794-2795.
7. (c) Zhang, Y.; Sigman, M. S. Org. Lett. 2006, 8, 5557-5560.
8. (d) Cornell, C. N.; Sigman, M. S. Org. Lett. 2006, 8, 4117-4120.
9. (e) Podhajsky, S. M.; Sigman, M. S. Organometallics 2007, 26, 5680-5686.
10. (f) For an example of a Pd-catalyzed coupled alcohol oxidation/alkene hydrogenation, see: Tsuchiya, Y.; Hamashima, Y.; Sodeoka, M. Org. Lett. 2006, 8, 4851-4854.
11. (a) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420.
12. (b) Stahl, S. S. Science 2005, 309, 1824-1826.
13. (c) Gligorich, K. M.; Sigman, M. S. Angew. Chem., Int. Ed. 2006, 45, 6612-6615.
14. Netherton, M. R.; Fu, G. C. Palladium-Catalyzed Cross-Coupling Reactions of Unactivated Alkyl Electrophiles with Organometallic Compounds. In Topics in Organometallic Chemistry; Springer-Verlag: Berlin, 2005; Vol. 14, pp 85-108.
15. (a) For an example of an oxidative Heck reaction with an arylstannane, see: Hirabayashi, K.; Ando, J.-I.; Nishihara, Y.; Mori, A.; Hiyama, T. Synlett 1999, 99-101.
16. (b) For a recent mechanistic study of the oxidative Heck reaction, see: Enquist, P.-A.; Nilsson, P.; Sjoberg, P.; Larhed, M. J. Org. Chem. 2006, 71, 8779-8786.
17. Hosokawa, T.; Ohta, T.; Kanayama, S.; Murahashi, S. J. Org. Chem. 1987, 52, 1758-1764.
18. (a) Sen, A.; Lai, T.-W. Inorg. Chem. 1984, 23, 3257-3258.
19. (b) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704-4734.
20. (a) For a Rh-catalyzed hydroarylation reaction of vinyl pyridine with an arylboronic acid, see: Lautens, M.: Roy, A.; Fukuoka, K.; Fagnou, K.; Martin-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358-5359.
21. For examples of Pd-catalyzed hydroarylations of Michael acceptors with arylstannanes, see: (b) Ohe, T.; Wakita, T.; Motofusa, S.; Cho, C. S.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 2000, 73, 2149-2155.
22. (c) Ohe, T.; Uemura, S. Tetrahedron Lett. 2002, 43, 1269-1271.
23. (d) Ohe, T.; Uemura, S. Bull. Chem. Soc. Jpn. 2003, 76, 1423-1431.
24. Boczon, W.; Pieczonka, G.; Wiewiorowski, M. Tetrahedron 1977, 33, 2565-2570.
25. Larson, E. J.; Pecoraro, V. L. J. Am. Chem. Soc. 1991, 113, 7809-7810.
26. See Supporting Information for details.
27. Steinhoff, B. A.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 4348-4355.
28. (a) For an example of a Lewis acid catalyzed hydroarylation reaction of alkenes, see: Rueping, M.; Nachtsheim, B. J.; Scheidt, T. Org. Lett. 2006, 8, 3717-3719.
29. (b) For a review of catalytic aromatic C-H transformations, see: Goj, L. A.; Gunnoe, T. B. Curr. Org. Chem. 2005, 9, 671-685.
30. For a review of the hydrovinylation reaction, see: RajanBabu, T. V. Chem. Rev. 2003, 103, 2845-2860.
31. For a recent review of the hydroacylation reaction, see: Jun, C.-H.; Jo, E.-A.; Park, J.-W. Eur. J. Org. Chem. 2007, 1869-1881.
32. The formation of 3a suggests a secondary pathway could be operating.
33. Johns, A. M.; Utsunomiya, M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 1828-1839.