Visible-Light-Induced Photoredox Construction of Trifluoromethylated Quaternary All-Carbon Centers and Tertiary Alcohols via C(sp3)–Si Bond Cleavage

Dandan Ma; Lingna Chang; Yue Cai; Dachang Bai

doi:10.1055/s-0040-1720139

Synthesis, Table of Contents

Synthesis 2025; 57(07): 1295-1305
DOI: 10.1055/s-0040-1720139

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Visible-Light-Induced Photoredox Construction of Trifluoromethylated Quaternary All-Carbon Centers and Tertiary Alcohols via C(sp³)–Si Bond Cleavage

Dandan Ma

,

Lingna Chang

,

Yue Cai

,

Dachang Bai∗

Abstract

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Abstract

The construction of trifluoromethylated quaternary carbon centers and tertiary alcohols is realized by organo-photoredox catalysis. The process proceeds via visible-light-induced C(sp³)–Si bond cleavage for the generation of α-trifluoromethylated benzyl radicals, which are readily trapped by electron-deficient alkenes with excellent regioselectivity for the construction of trifluoromethylated quaternary all-carbon centers. The α-difluoromethyl counterparts are also suitable for this radical conjugate addition. Furthermore, the in situ oxidation of these α-trifluoromethylated radicals with O₂ from air affords tertiary alcohols in high yields, which extends the Fleming–Tamao reaction to tertiary carbon systems.

Key words

visible-light-induced - trifluoromethylated quaternary carbon centers - tertiary alcohols - C(sp³)–Si bond cleavage - transition-metal-free

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