Chiral Borane-Catalyzed Asymmetric Hydrosilylation of 2,3,3-Trisubstituted 3 <i>H</i> -Indoles

An asymmetric Piers-type hydrosilylation of 2,3,3-trisubstituted 3<i>H</i>-indoles has been achieved for the first time using a chiral borane catalyst derived by the in situ hydroboration of a chiral monoalkene with HB(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub>. A broad range of optically active indolines were afforded in moderate to high yields with 60-95% ee.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-11-14
DOI
https://doi.org/10.1021/acs.joc.5c02315
Primary Topic
Organoboron and organosilicon chemistry
Type
article
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article

Chiral Borane-Catalyzed Asymmetric Hydrosilylation of 2,3,3-Trisubstituted 3 H -Indoles

Xiangqing Feng, Fuqu Zou, Haifeng Du
The Journal of Organic Chemistry
Organoboron and organosilicon chemistry
article

Chiral Borane-Catalyzed Asymmetric Hydrosilylation of 2,3,3-Trisubstituted 3 H -Indoles

Xiangqing Feng, Fuqu Zou, Haifeng Du
article en

Abstract

An asymmetric Piers-type hydrosilylation of 2,3,3-trisubstituted 3<i>H</i>-indoles has been achieved for the first time using a chiral borane catalyst derived by the in situ hydroboration of a chiral monoalkene with HB(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub>. A broad range of optically active indolines were afforded in moderate to high yields with 60-95% ee.

The Journal of Organic ChemistryVol. 90(47)
Chinese Academy of Sciences (CN), Beijing National Laboratory for Molecular Sciences (CN), Institute of Chemistry (CN), University of Chinese Academy of Sciences (CN)
Openalex Percentile: Top 74%
Organoboron and organosilicon chemistry
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