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Aniline Carbamates: A Versatile and Removable Motif for Palladium‐Catalyzed Directed CH Activation
Author(s) -
Uhlig Nick,
Li ChaoJun
Publication year - 2014
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.201403712
Subject(s) - aniline , palladium , chemistry , catalysis , aryl , carbamate , aniline compounds , selectivity , combinatorial chemistry , stereochemistry , organic chemistry , alkyl
The aniline carbamate is introduced as a new removable directing group for CH activation. Its versatility and ability as a directing group are demonstrated by its use in the ortho ‐arylation of a wide variety of aniline derivatives under palladium(II) catalysis, with symmetric diaryliodonium salts as aryl donors. The reaction differs from previously reported arylations in its selectivity and its mechanism, as elucidated by kinetic and isotopic experiments. The directing group can also be easily removed under a variety of conditions.