Regioselective α-Allylation of Cyclic Allylborates with Allylic Bromides

Allylic boron compounds are valuable nucleophiles for introducing allylic moieties into organic compounds. While numerous examples of γ-selective functionalization, such as the allylboration of carbonyl compounds, have been reported, α-selective carbon-carbon bond formation involving allylborates remains limited. In this study, α-selective allylation of cyclic allylborates was achieved using allylic bromides as carbon-based electrophiles. The reaction between cyclic allylborates and allylic bromides produced various allylboronates in moderate to good yields.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-03-31
DOI
https://doi.org/10.1021/acs.joc.5c00135
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
0.00

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article

Regioselective α-Allylation of Cyclic Allylborates with Allylic Bromides

Kazuhiko Semba, Tetsuaki Fujihara, Hiroyuki Murata, Go Yamagiwa
The Journal of Organic Chemistry
Asymmetric Synthesis and Catalysis
article

Regioselective α-Allylation of Cyclic Allylborates with Allylic Bromides

Kazuhiko Semba, Tetsuaki Fujihara, Hiroyuki Murata, Go Yamagiwa
article en

Abstract

Allylic boron compounds are valuable nucleophiles for introducing allylic moieties into organic compounds. While numerous examples of γ-selective functionalization, such as the allylboration of carbonyl compounds, have been reported, α-selective carbon-carbon bond formation involving allylborates remains limited. In this study, α-selective allylation of cyclic allylborates was achieved using allylic bromides as carbon-based electrophiles. The reaction between cyclic allylborates and allylic bromides produced various allylboronates in moderate to good yields.

The Journal of Organic ChemistryVol. 90(14)
Kyoto University (JP)
Japan Society for the Promotion of Science, Core Research for Evolutional Science and Technology
Openalex Percentile: Top 95%
Asymmetric Synthesis and Catalysis
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