Weak Bronsted base-promoted photoredox catalysis for C-H alkylation of heteroarenes mediated by triplet excited diaryl ketone

A weak Bronsted base-promoted photoredox catalysis has been developed for the direct C-H alpha-alkyla-tion of heteroarenes with cyclic and acyclic ethers. The high efficiency of this strategy is demonstrated by the mild reaction conditions, broad substrate scope, economical reagents and high regiose...

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Bibliographic Details
Published inTetrahedron letters Vol. 99; pp. 153846 - 153849
Main Authors Li, Lifan, Song, Xuyan, Qi, Mei-Fang, Sun, Bing
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 08.06.2022
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
Heteroarene
Diaryl ketone
ETHERS
ACID
ARYLATION
Br?nsted base
FREE-RADICAL REACTIONS
C(SP)-H
N-OXIDES
Photoredox
Alkylation
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Summary:A weak Bronsted base-promoted photoredox catalysis has been developed for the direct C-H alpha-alkyla-tion of heteroarenes with cyclic and acyclic ethers. The high efficiency of this strategy is demonstrated by the mild reaction conditions, broad substrate scope, economical reagents and high regioselectivity. With air as the sole oxidant, a set of alkylated heteroarenes were accessed smoothly. This strategy was also applied for late-stage functionalization of valuable vitamin E nicotinate and loratadine. (C) 2022 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.153846