Rhodium-catalyzed dehydrogenative borylation of cyclic alkenes

Chemical Communications

Volumn 46, Issue 6, 2010, Pages 907-909

  Kondoh, Azusa ^a   Jamison, Timothy F ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BORONIC ACID DERIVATIVE; CYCLIC 1 ALKENYLBORONIC ACID PINACOL ESTER; CYCLIC ALKENE; RHODIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEHYDROGENATION; DEHYDROGENATIVE BORYLATION; SUZUKI MIYAURA CROSS COUPLING; SUZUKI REACTION;

EID: 75649100867     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b921387b     Document Type: Article

References (26)

1. A. Suzuki J. Organomet. Chem. 1999 576 147 168
2. N. Miyaura A. Suzuki Chem. Rev. 1995 95 2457 2483
3. K. Smith and A. Pelter, in Comprehensive Organic Synthesis, ed., B. M. Trost, Pergamon Press, Oxford, UK, 1991, vol. 8, p. 703
4. T. Ohmura Y. Yamamoto N. Miyaura J. Am. Chem. Soc. 2000 122 4990 4991
5. I. Beletskaya A. Pelter Tetrahedron 1997 53 4957 5026
6. X. He J. F. Hartwig J. Am. Chem. Soc. 1996 118 1696 1702
7. S. Pereira M. Srebnik Organometallics 1995 14 3127 3128
8. Ed. N. Miyaura and K. Maruoka, in Synthesis of Organometallic Compounds, ed., S. Komiya, Wiley, Chichester, UK, 1997, p. 345
9. K. L. Billingsley S. L. Buchwald J. Org. Chem. 2008 73 5589 5591
10. K. L. Billingsley T. E. Barder S. L. Buchwald Angew. Chem., Int. Ed. 2007 46 5359 5363
11. J. Takagi K. Takahashi T. Ishiyama N. Miyaura J. Am. Chem. Soc. 2002 124 8001 8006
12. K. Takahashi J. Takagi T. Ishiyama N. Miyaura Chem. Lett. 2000 126 127
13. P. R. Eastwood Tetrahedron Lett. 2000 41 3705 3708
14. T. M. Boller J. M. Murphy M. Hapke T. Ishiyama N. Miyaura J. F. Hartwig J. Am. Chem. Soc. 2005 127 14263 14278
15. T. Ishiyama J. Takagi J. F. Hartwig N. Miyaura Angew. Chem., Int. Ed. 2002 41 3056 3058
16. T. Ishiyama J. Takagi K. Ishida N. Miyaura N. R. Anastasi J. F. Hartwig J. Am. Chem. Soc. 2002 124 390 391
17. J.-Y. Cho M. K. Tse D. Holmes R. E. Maleczka Jr. M. R. Smith III Science 2002 295 305 308
18. C. N. Iverson M. R. Smith III J. Am. Chem. Soc. 1999 121 7696 7697
19. N. Miyaura, in Catalytic Heterofunctionalization, ed., A. Togni, and, H. Grützmacher, Wiley-VCH, Weinheim, Germany, 2001, p. 10
20. I. A. I. Mkhalid R. B. Coapes S. N. Edes D. N. Coventry F. E. S. Souza R. LI. Thomas J. J. Hall S.-W. Bi Z. Lin T. B. Marder Dalton Trans. 2008 1055 1064
21. T. Ohmura Y. Takasaki H. Furukawa M. Suginome Angew. Chem., Int. Ed. 2009 48 2372 2375
22. A. Caballero S. Sabo-Etienne Organometallics 2007 26 1191 1195
23. T. Kikuchi J. Takagi H. Isou T. Ishiyama N. Miyaura Chem.-Asian J. 2008 3 2082 2090
24. T. Kikuchi J. Takagi T. Ishiyama N. Miyaura Chem. Lett. 2008 37 664 665
25. V. J. Olsson K. J. Szabó Angew. Chem., Int. Ed. 2007 46 6891 6893
26. 2 provided similar results to Xantphos Under the same reaction conditions, the acyclic internal alkenes cis-4-octene and trans-4-octene afforded a complex mixture of products. The reactions of substituted cyclic alkenes such as 1-methylcyclohexene and 3-methylcyclohexene also gave a complex mixture of the products, and α-methylstyrene and methylenecyclohexene provided the corresponding products in moderate yields (60% and 40%, respectively)