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Nickel‐Catalyzed Benzylation of C−H Bonds in Aromatic Amides with Benzyltrimethylammonium Halides
Author(s) -
Sasagawa Akane,
Yamaguchi Mao,
Ano Yusuke,
Chatani Naoto
Publication year - 2017
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.201700044
Subject(s) - chemistry , halide , moiety , catalysis , nickel , alkylation , medicinal chemistry , denticity , derivative (finance) , organic chemistry , functional group , combinatorial chemistry , crystal structure , financial economics , economics , polymer
Abstract Nickel‐catalyzed benzylation reactions of C−H bonds in aromatic amides with benzyltrimethylammonium halides are developed by using a 5‐chloro‐8‐aminoquinoline derivative as a bidentate directing group. Benzylation occurs selectively at the ortho‐C−H bonds in aromatic amides, and no methylation was detected. The presence of a 5‐chloro‐8‐aminoquinoline moiety is essential for the success of this reaction, in which a variety of functional groups can be tolerated.