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Nitrile as a Versatile Directing Group for C( sp 2 )–H Functionalizations
Author(s) -
Ping Yuanyuan,
Wang Liping,
Ding Qiuping,
Peng Yiyuan
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700684
Subject(s) - regioselectivity , chemistry , nitrile , iridium , halogenation , rhodium , functional group , hydroxylation , palladium , catalysis , combinatorial chemistry , ruthenium , group (periodic table) , organic chemistry , medicinal chemistry , enzyme , polymer
The one‐step direct regioselective functionaliztion of inert C( sp 2 )–H bonds is an efficient and sustainable methodology for the synthesis of a variety of useful natural products and pharmaceutical intermediates. A range of functional groups have been widely used as directing group for various regioselective transformations. Among these, the weakly coordinating nitrile group has attracted much attention because it is a transformable, easily installed and readily removed directing group, which can be easily converted into a number of different functional groups, such as carboxyl, carbamoyl, aminomethyl, carbonyl, and heterocyclic functionalities. This review describes recent advances in nitrile‐directed C–H functionalizations catalyzed by palladium(II), ruthenium(II), rhodium(III) and iridium(I) catalysts. The review is divided into sections related to ortho ‐, meta ‐, and para ‐C–H bond functionalizations, which are subdivided according to reaction type (olefination, arylation, halogenation, hydroxylation and acetoxylation).