Trifluoromethylborylation of Unactivated Alkenes via an Electron Donor–Acceptor (EDA) Complex

This communication describes a straightforward method for the trifluoromethylborylation of unactivated alkenes. The reaction proceeds through the formation of an electron donor-acceptor (EDA) complex between a trifluoromethylthiophenium salt and bis(catechol)diboron under broad-spectrum white-light irradiation. Due to the mild reaction conditions, the trifluoromethylborylation tolerates a wide range of functional groups, including esters, acids, alcohols, epoxides, and a variety of heterocycles. The reaction does not require a transition metal catalyst and tolerates both air and moisture, proceeding under concentrated conditions (1 M). Mechanistic studies provide a general reaction coordinate for the overall transformation.

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Publication Details

Journal
Organic Letters
Published
2025-09-10
DOI
https://doi.org/10.1021/acs.orglett.5c03452
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Trifluoromethylborylation of Unactivated Alkenes via an Electron Donor–Acceptor (EDA) Complex

Silas P. Cook, H. Nguyen
Organic Letters
Fluorine in Organic Chemistry
article

Trifluoromethylborylation of Unactivated Alkenes via an Electron Donor–Acceptor (EDA) Complex

Silas P. Cook, H. Nguyen
article en

Abstract

This communication describes a straightforward method for the trifluoromethylborylation of unactivated alkenes. The reaction proceeds through the formation of an electron donor-acceptor (EDA) complex between a trifluoromethylthiophenium salt and bis(catechol)diboron under broad-spectrum white-light irradiation. Due to the mild reaction conditions, the trifluoromethylborylation tolerates a wide range of functional groups, including esters, acids, alcohols, epoxides, and a variety of heterocycles. The reaction does not require a transition metal catalyst and tolerates both air and moisture, proceeding under concentrated conditions (1 M). Mechanistic studies provide a general reaction coordinate for the overall transformation.

Organic LettersVol. 27(37)
Indiana University Bloomington (US)
Openalex Percentile: Top 82%
Fluorine in Organic Chemistry
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