Tertiary Amines Acting as Alkyl Radical Equivalents Enabled by a P/N Heteroleptic Cu(I) Photosensitizer

An unprecedented exploration of tertiary amines as alkyl radical equivalents for cross-coupling with aromatic alkynes to access allylarenes has been achieved by a P/N heteroleptic Cu­(I)-based photosensitizer under photoredox catalysis conditions. Mechanistic studies reveal that the reaction might u...

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Published inOrganic letters Vol. 22; no. 22; pp. 8888 - 8893
Main Authors Zheng, Limeng, Jiang, Qinfang, Bao, Hanyang, Zhou, Bingwei, Luo, Shu-Ping, Jin, Hongwei, Wu, Huayue, Liu, Yunkui
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.11.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
C-H ALKYLATION
PHOTOCATALYTIC HYDROGEN-PRODUCTION
WATER REDUCTION
METALLAPHOTOREDOX CATALYSIS
CROSS-COUPLINGS
LIGHT
SINGLE-ELECTRON TRANSMETALATION
HECK REACTION
COPPER-BASED PHOTOSENSITIZERS
PHOTOREDOX CATALYSIS
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Summary:An unprecedented exploration of tertiary amines as alkyl radical equivalents for cross-coupling with aromatic alkynes to access allylarenes has been achieved by a P/N heteroleptic Cu­(I)-based photosensitizer under photoredox catalysis conditions. Mechanistic studies reveal that the reaction might undergo radical addition of in situ-generated α-amino radical intermediates to alkynes followed by 1,5-hydrogen transfer, C–N bond cleavage, and concomitant isomerization of the resulting allyl radical species.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03236