Nickel-catalyzed addition of organoboronates to 1,2-dienes and the corresponding three-component reaction with an alkyne

Advanced Synthesis and Catalysis

Volumn 348, Issue 7-8, 2006, Pages 837-840

  Takahashi, Go ^a   Shirakawa, Eiji ^b   Tsuchimoto, Teruhisa ^a   Kawakami, Yusuke ^a  

^a JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Alkynes; Allenes; Arylboronates; Hydroalkenylation; Hydroarylation; Nickel

Indexed keywords

EID: 33744799685     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200505445     Document Type: Article

References (19)

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14. Ma and co-workers also have reported the hydroarylation of 1,2-dienes, where a catalytic or stoichiometric amount of acetic acid acts as an indispensable activator, see: a) S. Ma, N. Jiao, L. Ye, Chem. Eur. J. 2003, 9, 6049-6056;
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16. An intramolecular version of the reaction using a palladium catalyst, 1,6-allenynes and arylboronic acids has recently been published: A. K. Gupta, C. Y. Rhim, C. H. Oh, Tetrahedron Lett. 2005, 46, 2247-2250.
17. We have already reported the nickel-catalyzed tandem carbostannylation of 1,2-dienes and alkynes with alkynylstannanes, see: E. Shirakawa, Y. Yamamoto, Y. Nakao, S. Oda, T. Tsuchimoto, T. Hiyama, Angew. Chem. Int. Ed. 2004, 43, 3448-3451.
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19. 3 is more effective than bidentate aminophosphine AP in the three-component reaction.