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Issue 31, 2014
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Studies on copper(I)-catalyzed highly regio- and stereo-selective hydroboration of alkynamides

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Abstract

The copper(I)-catalyzed hydroboration of alkynamides with B2pin2 afforded the alkenamide boronates in 66% to nearly quantitative yields with high regio- and stereo-selectivity. It was interesting to note that the regio-selectivity of the reaction is opposite to that observed in the carbometallation reaction of alkynamides, and the resulting alkenyl boronates provided access to α,β-disubstituted (Z)-alkenamides through further elaboration.

Graphical abstract: Studies on copper(i)-catalyzed highly regio- and stereo-selective hydroboration of alkynamides

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Publication details

The article was received on 13 May 2014, accepted on 17 Jun 2014 and first published on 02 Jul 2014


Article type: Paper
DOI: 10.1039/C4OB00979G
Citation: Org. Biomol. Chem., 2014,12, 5945-5953
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    Studies on copper(I)-catalyzed highly regio- and stereo-selective hydroboration of alkynamides

    G. He, S. Chen, Q. Wang, H. Huang, Q. Zhang, D. Zhang, R. Zhang and H. Zhu, Org. Biomol. Chem., 2014, 12, 5945
    DOI: 10.1039/C4OB00979G

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