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Weak O ‐Assistance Outcompeting Strong N , N ‐Bidentate Directing Groups in Copper‐Catalyzed C−H Chalcogenation
Author(s) -
Cera Gianpiero,
Ackermann Lutz
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201601821
Subject(s) - denticity , copper , catalysis , scope (computer science) , selectivity , substrate (aquarium) , chemistry , stereochemistry , crystallography , computer science , crystal structure , organic chemistry , biology , programming language , ecology
A copper‐mediated C−H chalcogenation of triazoles has been achieved by weak coordination. The user‐friendly protocol showed high functional‐group tolerance and ample substrate scope, yielding fully substituted 1,2,3‐triazoles with complete positional site‐selectivity. The C−H selenylation could likewise be achieved by means of copper catalysis. Our findings highlight for the first time that weak O ‐coordination can outcompete the strong N , N ‐bidentate coordination mode in C−H functionalization technology.