Palladium-catalyzed addition of cyanoboranes to alkynes: Regio- and stereoselective synthesis of α,β-unsaturated β-boryl nitriles

Angewandte Chemie - International Edition

Volumn 44, Issue 16, 2005, Pages 2380-2382

  Suginome, Michinori ^a,b   Yamamoto, Akihiko ^a   Murakami, Masahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Alkynes; Boron; Cyanides; Palladium; Regioselectivity

Indexed keywords

ADDITION REACTIONS; CATALYSIS; NITRILE RESINS; PALLADIUM; SYNTHESIS (CHEMICAL);

ALKYNES; ARYL GROUP; CYANOBORANES; CYANOBORATION;

HYDROCARBONS;

ALKYNE; BORANE DERIVATIVE; NITRILE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY;

ALKYNES; BORANES; CATALYSIS; NITRILES; PALLADIUM;

EID: 18044364253     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462961     Document Type: Article

References (27)

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14. For related additions of cyanide-containing o bonds to alkynes, see: a) hydrocyanation: R. Jackson, C. G. Lovel, J. Chem. Soc. Chem. Commun. 1982, 1231; b) cyanosilylation: N. Chatani, T. Hanafusa, J. Chem. Soc. Chem. Commun. 1985, 838; c) N. Chatani, T. Takeyasu, N. Horiuchi, T. Hanafusa, J. Org. Chem. 1988, 53, 3539; d) M. Suginome, H. Kinugasa, Y. Ito, Tetrahedron Lett. 1994, 35, 8635; e) cyanostannation: Y. Obora, A. S. Baleta, M. Tokunaga, Y. Tsuji, J. Organomet. Chem. 2002, 660, 173; f) acyl cyanation: K. Nozaki, N. Sato, H. Takaya, J. Org. Chem. 1994, 59, 2679; g) aryl cyanation: Y. Nakao, S. Oda, T. Hiyama, J. Am. Chem. Soc. 2004, 126, 13904.
15. For related additions of cyanide-containing o bonds to alkynes, see: a) hydrocyanation: R. Jackson, C. G. Lovel, J. Chem. Soc. Chem. Commun. 1982, 1231; b) cyanosilylation: N. Chatani, T. Hanafusa, J. Chem. Soc. Chem. Commun. 1985, 838; c) N. Chatani, T. Takeyasu, N. Horiuchi, T. Hanafusa, J. Org. Chem. 1988, 53, 3539; d) M. Suginome, H. Kinugasa, Y. Ito, Tetrahedron Lett. 1994, 35, 8635; e) cyanostannation: Y. Obora, A. S. Baleta, M. Tokunaga, Y. Tsuji, J. Organomet. Chem. 2002, 660, 173; f) acyl cyanation: K. Nozaki, N. Sato, H. Takaya, J. Org. Chem. 1994, 59, 2679; g) aryl cyanation: Y. Nakao, S. Oda, T. Hiyama, J. Am. Chem. Soc. 2004, 126, 13904.
16. For related additions of cyanide-containing o bonds to alkynes, see: a) hydrocyanation: R. Jackson, C. G. Lovel, J. Chem. Soc. Chem. Commun. 1982, 1231; b) cyanosilylation: N. Chatani, T. Hanafusa, J. Chem. Soc. Chem. Commun. 1985, 838; c) N. Chatani, T. Takeyasu, N. Horiuchi, T. Hanafusa, J. Org. Chem. 1988, 53, 3539; d) M. Suginome, H. Kinugasa, Y. Ito, Tetrahedron Lett. 1994, 35, 8635; e) cyanostannation: Y. Obora, A. S. Baleta, M. Tokunaga, Y. Tsuji, J. Organomet. Chem. 2002, 660, 173; f) acyl cyanation: K. Nozaki, N. Sato, H. Takaya, J. Org. Chem. 1994, 59, 2679; g) aryl cyanation: Y. Nakao, S. Oda, T. Hiyama, J. Am. Chem. Soc. 2004, 126, 13904.
17. For related additions of cyanide-containing o bonds to alkynes, see: a) hydrocyanation: R. Jackson, C. G. Lovel, J. Chem. Soc. Chem. Commun. 1982, 1231; b) cyanosilylation: N. Chatani, T. Hanafusa, J. Chem. Soc. Chem. Commun. 1985, 838; c) N. Chatani, T. Takeyasu, N. Horiuchi, T. Hanafusa, J. Org. Chem. 1988, 53, 3539; d) M. Suginome, H. Kinugasa, Y. Ito, Tetrahedron Lett. 1994, 35, 8635; e) cyanostannation: Y. Obora, A. S. Baleta, M. Tokunaga, Y. Tsuji, J. Organomet. Chem. 2002, 660, 173; f) acyl cyanation: K. Nozaki, N. Sato, H. Takaya, J. Org. Chem. 1994, 59, 2679; g) aryl cyanation: Y. Nakao, S. Oda, T. Hiyama, J. Am. Chem. Soc. 2004, 126, 13904.
18. For related additions of cyanide-containing o bonds to alkynes, see: a) hydrocyanation: R. Jackson, C. G. Lovel, J. Chem. Soc. Chem. Commun. 1982, 1231; b) cyanosilylation: N. Chatani, T. Hanafusa, J. Chem. Soc. Chem. Commun. 1985, 838; c) N. Chatani, T. Takeyasu, N. Horiuchi, T. Hanafusa, J. Org. Chem. 1988, 53, 3539; d) M. Suginome, H. Kinugasa, Y. Ito, Tetrahedron Lett. 1994, 35, 8635; e) cyanostannation: Y. Obora, A. S. Baleta, M. Tokunaga, Y. Tsuji, J. Organomet. Chem. 2002, 660, 173; f) acyl cyanation: K. Nozaki, N. Sato, H. Takaya, J. Org. Chem. 1994, 59, 2679; g) aryl cyanation: Y. Nakao, S. Oda, T. Hiyama, J. Am. Chem. Soc. 2004, 126, 13904.
19. For related additions of cyanide-containing o bonds to alkynes, see: a) hydrocyanation: R. Jackson, C. G. Lovel, J. Chem. Soc. Chem. Commun. 1982, 1231; b) cyanosilylation: N. Chatani, T. Hanafusa, J. Chem. Soc. Chem. Commun. 1985, 838; c) N. Chatani, T. Takeyasu, N. Horiuchi, T. Hanafusa, J. Org. Chem. 1988, 53, 3539; d) M. Suginome, H. Kinugasa, Y. Ito, Tetrahedron Lett. 1994, 35, 8635; e) cyanostannation: Y. Obora, A. S. Baleta, M. Tokunaga, Y. Tsuji, J. Organomet. Chem. 2002, 660, 173; f) acyl cyanation: K. Nozaki, N. Sato, H. Takaya, J. Org. Chem. 1994, 59, 2679; g) aryl cyanation: Y. Nakao, S. Oda, T. Hiyama, J. Am. Chem. Soc. 2004, 126, 13904.
20. Caution! The handling cyanoboranes requires special care to avoid inhalation of hydrogen cyanide, which may be generated by the hydrolysis of the cyanoboranes. Although the eyanoboranes can be handled in air for short periods, for example, to be weighed out, all operations should be carried out in a fume hood.
21. 3, with the corresponding diamines in the presence of a base.
22. 3, with the corresponding diamines in the presence of a base.
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