Copper-Catalyzed Regioselective Dihydroboration of Alkynes to Construct <i>gem</i>-Diborylalkanes

We develop herein an efficient copper-catalyzed dihydroboration of alkynes with HBpin to synthesize <i>gem</i>-diborylalkanes. This catalytic process features a broad substrate scope, good functional group tolerance, and excellent regioselectivity. Notably, the gram-scale reaction and further product derivatizations demonstrate the practicality of this protocol. Preliminary mechanistic studies indicate that the process involves the hydroboration of the alkyne and the vinylboronate intermediate.

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Publication Details

Journal
Organic Letters
Published
2025-03-20
DOI
https://doi.org/10.1021/acs.orglett.5c00943
Citations
6
Primary Topic
Organoboron and organosilicon chemistry
Type
article
Field-Weighted Citation Impact
5.62

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article

Copper-Catalyzed Regioselective Dihydroboration of Alkynes to Construct gem-Diborylalkanes

Wanxiang Zhao, Zheming Liu, Wenke Dong, Guanglu Liu et al.
6 citations
Organic Letters
Organoboron and organosilicon chemistry
5.62
article

Copper-Catalyzed Regioselective Dihydroboration of Alkynes to Construct gem-Diborylalkanes

Wanxiang Zhao, Zheming Liu, Wenke Dong, Guanglu Liu, Zhenyuan Zhang, Minghao Zhang, Y.-B. Wei
article en
6 citations

Abstract

We develop herein an efficient copper-catalyzed dihydroboration of alkynes with HBpin to synthesize <i>gem</i>-diborylalkanes. This catalytic process features a broad substrate scope, good functional group tolerance, and excellent regioselectivity. Notably, the gram-scale reaction and further product derivatizations demonstrate the practicality of this protocol. Preliminary mechanistic studies indicate that the process involves the hydroboration of the alkyne and the vinylboronate intermediate.

Organic LettersVol. 27(12)
Hunan University (CN), Zhoukou Normal University (CN)
Zhoukou Normal University, National Natural Science Foundation of China, Science and Technology Program of Hunan Province
Openalex Percentile: Top 5%
Organoboron and organosilicon chemistry
5.62
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Copper-Catalyzed Regioselective Dihydroboration of Alkynes to Construct <i>gem</i>-Diborylalkanes — Wanxiang Zhao, Zheming Liu, et al. · Organic Letters (2025) | TGRS Research Map | TGRS