The Stabilized Cation Pool Method: Metal- and Oxidant-Free Benzylic C–H/Aromatic C–H Cross-Coupling

Electrochemical oxidation of toluene derivatives in the presence of a sulfilimine gave benzylaminosulfonium ions as stabilized benzyl cation pools, which reacted with subsequently added aromatic nucleophiles to give the corresponding cross-coupling products. The transformation serves as a powerful m...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 138; no. 27; pp. 8400 - 8403
Main Authors Hayashi, Ryutaro, Shimizu, Akihiro, Yoshida, Jun-ichi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 13.07.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
AMINATION
CARBOCATIONS
SEARCH
AMINES
ARYLATION
ANODIC OXIDATIONS
BOND FORMATION
GENERATION
FORMYLCHROMONE DERIVATIVES
ECONOMY
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Summary:Electrochemical oxidation of toluene derivatives in the presence of a sulfilimine gave benzylaminosulfonium ions as stabilized benzyl cation pools, which reacted with subsequently added aromatic nucleophiles to give the corresponding cross-coupling products. The transformation serves as a powerful metal- and chemical-oxidant-free method for benzylic C–H/aromatic C–H cross-coupling. The method has been successfully applied to synthesis of TP27, an inhibitor of PTPase.
Bibliography:KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b05273