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

Guangke He; Shan Chen; Qiang Wang; Hai Huang; Qijun Zhang; Dongming Zhang; Rong Zhang; Hongjun Zhu

doi:10.1039/c4ob00979g

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

Guangke He, Shan Chen, Qiang Wang, Hai Huang, Qijun Zhang, Dongming Zhang, Rong Zhang, Hongjun Zhu

School of Chemistry and Moleculai Engineering

Nanjing Tech University

Research output: Contribution to journal › Article › peer-review

40 Scopus citations

Abstract

The copper(i)-catalyzed hydroboration of alkynamides with B ₂pin₂ 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,-disubstituted (Z)-alkenamides through further elaboration. This journal is

Original language	English
Pages (from-to)	5945-5953
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	31
DOIs	https://doi.org/10.1039/c4ob00979g
State	Published - 21 Aug 2014

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abstract = "The copper(i)-catalyzed hydroboration of alkynamides with B 2pin2 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,-disubstituted (Z)-alkenamides through further elaboration. This journal is",

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AU - He, Guangke

AU - Chen, Shan

AU - Wang, Qiang

AU - Huang, Hai

AU - Zhang, Qijun

AU - Zhang, Dongming

AU - Zhang, Rong

AU - Zhu, Hongjun

PY - 2014/8/21

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AB - The copper(i)-catalyzed hydroboration of alkynamides with B 2pin2 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,-disubstituted (Z)-alkenamides through further elaboration. This journal is

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ER -

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

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