Direct C(sp3)–H Arylation of Unprotected Benzyl Anilines and Alkylarenes by Organocatalysis under Visible Light

Reported herein is direct C­(sp3)–H arylation of unprotected benzyl anilines and alkylarenes via consecutive photoinduced electron transfer by visible light irradiation. Reductive quenching cycles and radical–radical cross-coupling were involved, and electron paramagnetic resonance experiments provi...

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Published inOrganic letters Vol. 26; no. 1; pp. 304 - 309
Main Authors Huang, Cheng, Xiao, Peng, Ye, Zhong-Ming, Wang, Chen-Lu, Kang, Chen, Tang, Sheng, Wei, Zhenhong, Cai, Hu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 12.01.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACTIVATION
C-H ARYLATION
REDUCTION
PHOTOREDOX
ALKYLATION
BONDS
ATOM-TRANSFER
POTENTIALS
SINGLE-ELECTRON TRANSFER
CATALYZED ARYLATION
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Summary:Reported herein is direct C­(sp3)–H arylation of unprotected benzyl anilines and alkylarenes via consecutive photoinduced electron transfer by visible light irradiation. Reductive quenching cycles and radical–radical cross-coupling were involved, and electron paramagnetic resonance experiments provide evidence for the formation of radical intermediates formed in situ. The protocol highlights transition metal free, external oxidant free, broad substrate scope, and high efficiency (>60 examples, up to 96%).
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.3c03980