Direct Deoxyboration of Alkyl Alcohols

This study describes the direct activation of typical alkyl alcohols by neutral boron radicals, followed by a realistic boronization reaction scheme. The reaction in question necessitates an effective reagent that can swiftly activate the alcohol hydroxyl group to produce radicals. This is essential for preventing coordination of the alcohol hydroxyl group to the boron reagent. This study presents an efficient photocatalytic method for generating boron radicals from cost-effective and readily accessible sodium tetraphenylboron. This mechanism facilitates activation of the alcohol hydroxyl group for dehydroxylation and boronization. Dehydroxylation does not require prior activation of the alcohol, improves the reaction efficiency, and yields excellent results for most alcohol substrates.

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Publication Details

Journal
Organic Letters
Published
2025-06-06
DOI
https://doi.org/10.1021/acs.orglett.5c01743
Citations
5
Primary Topic
Chemical Synthesis and Analysis
Type
article
Field-Weighted Citation Impact
4.03

Funders

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article

Direct Deoxyboration of Alkyl Alcohols

Y.Y. Chen, Lingyun Huang, Hanbo Chen, Ruoxi Yu et al.
5 citations
Organic Letters
Chemical Synthesis and Analysis
4.03
article

Direct Deoxyboration of Alkyl Alcohols

Y.Y. Chen, Lingyun Huang, Hanbo Chen, Ruoxi Yu, Qi Pan
article en
5 citations

Abstract

This study describes the direct activation of typical alkyl alcohols by neutral boron radicals, followed by a realistic boronization reaction scheme. The reaction in question necessitates an effective reagent that can swiftly activate the alcohol hydroxyl group to produce radicals. This is essential for preventing coordination of the alcohol hydroxyl group to the boron reagent. This study presents an efficient photocatalytic method for generating boron radicals from cost-effective and readily accessible sodium tetraphenylboron. This mechanism facilitates activation of the alcohol hydroxyl group for dehydroxylation and boronization. Dehydroxylation does not require prior activation of the alcohol, improves the reaction efficiency, and yields excellent results for most alcohol substrates.

Organic LettersVol. 27(24)
Zhejiang Sci-Tech University (CN)
China Postdoctoral Science Foundation, Zhejiang Sci-Tech University, Natural Science Foundation of Zhejiang Province
Openalex Percentile: Top 6%
Chemical Synthesis and Analysis
4.03
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Direct Deoxyboration of Alkyl Alcohols — Y.Y. Chen, Lingyun Huang, et al. · Organic Letters (2025) | TGRS Research Map | TGRS