Uncovering the Reactivity of Direct Photoredox Catalyzed α-C–H Alkylation of Alcohols: A Boron-Free Procedure

Alcohol functionalization is an important class of pharmaceutically relevant transformations that have increasingly been achieved through photoredox-hydrogen atom transfer catalysis. Many methods rely on exogenous bond-weakening activators such as boron-based catalysts. Herein, a reported hemiboronic acid catalyst was shown to dynamically interact with alcohols, however, with no effect on the efficiency or stereoselectivity of the α-C-H alkylation of alcohols. A simplified procedure affords products in yields of 18-95% without a boron cocatalyst.

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Publication Details

Journal
Organic Letters
Published
2026-02-24
DOI
https://doi.org/10.1021/acs.orglett.6c00235
Primary Topic
Organoboron and organosilicon chemistry
Type
article
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article

Uncovering the Reactivity of Direct Photoredox Catalyzed α-C–H Alkylation of Alcohols: A Boron-Free Procedure

Dennis G. Hall, Geneviève O’Keefe
Organic Letters
Organoboron and organosilicon chemistry
article

Uncovering the Reactivity of Direct Photoredox Catalyzed α-C–H Alkylation of Alcohols: A Boron-Free Procedure

Dennis G. Hall, Geneviève O’Keefe
article en

Abstract

Alcohol functionalization is an important class of pharmaceutically relevant transformations that have increasingly been achieved through photoredox-hydrogen atom transfer catalysis. Many methods rely on exogenous bond-weakening activators such as boron-based catalysts. Herein, a reported hemiboronic acid catalyst was shown to dynamically interact with alcohols, however, with no effect on the efficiency or stereoselectivity of the α-C-H alkylation of alcohols. A simplified procedure affords products in yields of 18-95% without a boron cocatalyst.

Organic LettersVol. 28(9)
Centennial College (CA)
Openalex Percentile: Top 43%
Organoboron and organosilicon chemistry
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