Ni-Catalyzed Remote Radical/Cross-Electrophile Coupling Cascade for Selective C(sp3)–H Arylation

An innovative 1,5-HAT cascade strategy has been advanced for the nickel-catalyzed distal arylation via cross-electrophile coupling. Through specific migration, the remote C­(sp3)–H bond is regioselectively activated, and Ar–I as the available electrophile is used for the construction of the C­(sp3)–...

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Published inOrganic letters Vol. 24; no. 12; pp. 2399 - 2403
Main Authors Wen, Ya-Ting, Kong, Xiang-Tao, Liu, Hong-Chao, Wang, Cui-Tian, Wei, Wan-Xu, Wang, Bin, Liu, Xue-Yuan, Liang, Yong-Min
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.04.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALPHA-AMINO-ACIDS
H BOND FUNCTIONALIZATION
ALKYLATION
VINYLATION
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Summary:An innovative 1,5-HAT cascade strategy has been advanced for the nickel-catalyzed distal arylation via cross-electrophile coupling. Through specific migration, the remote C­(sp3)–H bond is regioselectively activated, and Ar–I as the available electrophile is used for the construction of the C­(sp3)–C­(sp2) bond. This method also has broad applicability for benzylic and aliphatic N-fluorocarboxamides with yields up to 80%. Furthermore, a series of control experiments demonstrated that this reaction is probably initiated by a radical process.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00666