Nickel-Catalyzed 1,1-Carboboration of Polysubstituted Internal Alkenes

Herein, we report a nickel-catalyzed 1,1-carboboration of di- and trisubstituted alkenyl boronates through a chain-walking strategy. This reaction effectively addresses the polarity-mismatch problem via ligand control, enabling the coupling of various carbon-based electrophiles while accommodating a broad range of functional groups. The approach yields diverse tetrasubstituted carbon <i>gem</i>-diboronate derivatives with exceptional regioselectivity. The synthetic utility of this method is further demonstrated through the concise synthesis of high-value bioactive molecules.

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Publication Details

Journal
Organic Letters
Published
2025-04-01
DOI
https://doi.org/10.1021/acs.orglett.5c00654
Citations
3
Primary Topic
Organoboron and organosilicon chemistry
Type
article
Field-Weighted Citation Impact
2.81

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article

Nickel-Catalyzed 1,1-Carboboration of Polysubstituted Internal Alkenes

Guoyin Yin, Yu Liu, Shiyang Wang, Yao Tong et al.
3 citations
Organic Letters
Organoboron and organosilicon chemistry
2.81
article

Nickel-Catalyzed 1,1-Carboboration of Polysubstituted Internal Alkenes

Guoyin Yin, Yu Liu, Shiyang Wang, Yao Tong, Yangyang Li
article en
3 citations

Abstract

Herein, we report a nickel-catalyzed 1,1-carboboration of di- and trisubstituted alkenyl boronates through a chain-walking strategy. This reaction effectively addresses the polarity-mismatch problem via ligand control, enabling the coupling of various carbon-based electrophiles while accommodating a broad range of functional groups. The approach yields diverse tetrasubstituted carbon <i>gem</i>-diboronate derivatives with exceptional regioselectivity. The synthetic utility of this method is further demonstrated through the concise synthesis of high-value bioactive molecules.

Organic LettersVol. 27(14)
Wuhan University (CN), Advanced Institute of Materials Science (JP), Changchun University of Technology (CN)
National Natural Science Foundation of China, People's Government of Jilin Province, Fundamental Research Funds for the Central Universities
Openalex Percentile: Top 11%
Organoboron and organosilicon chemistry
2.81
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