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Synfacts 2007(2): 0187-0187  
DOI: 10.1055/s-2006-955847
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Addition of Alkynylboranes to Alkynes

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
M. Suginome*, M. Shirakura, A. Yamamoto
Kyoto University, Japan
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Publication History

Publication Date:
23 January 2007 (online)

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Significance

Organoboranes are valuable synthetic intermediates in synthesis, and this report describes the stereoselective addition (cis) of alkynylboranes to alkynes. Pd catalysis did not afford any alkynylboration product while Ni(cod)2 proved to be the optimal catalyst. Of the many phosphine ligands tested PCy3 provided the best results while PMe3 showed no activity. Slow addition of the alkyne to the alkynylborane proved necessary to reduce oligomerization of the alkyne. Another attractive feature of this protocol is the regio­selective addition to unsymmetrical alkynes.