Copper-Catalyzed C–B(sp<sup>3</sup>) Bond Formation through the Intermediacy of Cu–B(sp<sup>3</sup>) Complex

The vast majority of transition metal (TM) catalyzed borylative transformations rely on TM-B(sp<sup>2</sup>) complexes. Contrastingly, the chemistry of TM-B(sp<sup>3</sup>) species and their potential in catalytic borylation remain surprisingly underdeveloped, due probably to the lack of suitable boron(sp<sup>3</sup>) reagents. Herein, we employ our recently developed sp<sup>2</sup>-sp<sup>3</sup> diboron reagent to successfully enable a copper-catalyzed hydroboration of allenes for C-B(sp<sup>3</sup>) bond formation. A comprehensive mechanistic study, including the isolation and structural characterization of a Cu-B(sp<sup>3</sup>) complex, substantiates the presence of a Cu-B(sp<sup>3</sup>) intermediate in the catalytic cycle.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2025-04-15
DOI
https://doi.org/10.1021/jacs.5c00974
Citations
12
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
11.23
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article

Copper-Catalyzed C–B(sp3) Bond Formation through the Intermediacy of Cu–B(sp3) Complex

Linlin Wu, Stephen Lam, Hairong Lyu, Zhanqiang Ye et al.
12 citations
Journal of the American Chemical Society
Catalytic Cross-Coupling Reactions
11.23
article

Copper-Catalyzed C–B(sp3) Bond Formation through the Intermediacy of Cu–B(sp3) Complex

Linlin Wu, Stephen Lam, Hairong Lyu, Zhanqiang Ye, Chun Yin Kwok
article en
12 citations

Abstract

The vast majority of transition metal (TM) catalyzed borylative transformations rely on TM-B(sp<sup>2</sup>) complexes. Contrastingly, the chemistry of TM-B(sp<sup>3</sup>) species and their potential in catalytic borylation remain surprisingly underdeveloped, due probably to the lack of suitable boron(sp<sup>3</sup>) reagents. Herein, we employ our recently developed sp<sup>2</sup>-sp<sup>3</sup> diboron reagent to successfully enable a copper-catalyzed hydroboration of allenes for C-B(sp<sup>3</sup>) bond formation. A comprehensive mechanistic study, including the isolation and structural characterization of a Cu-B(sp<sup>3</sup>) complex, substantiates the presence of a Cu-B(sp<sup>3</sup>) intermediate in the catalytic cycle.

Journal of the American Chemical SocietyVol. 147(18)
Central South University (CN), Chinese University of Hong Kong (HK), Interface (United States) (US)
Openalex Percentile: Top 1%
Catalytic Cross-Coupling Reactions
11.23
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Copper-Catalyzed C–B(sp<sup>3</sup>) Bond Formation through the Intermediacy of Cu–B(sp<sup>3</sup>) Complex — Linlin Wu, Stephen Lam, et al. · Journal of the American Chemical Society (2025) | TGRS Research Map | TGRS