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A Simple and Versatile Amide Directing Group for C−H Functionalizations
Author(s) -
Zhu RuYi,
Farmer Marcus E.,
Chen YanQiao,
Yu JinQuan
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201600791
Subject(s) - group (periodic table) , moiety , amide , context (archaeology) , functional group , chemistry , covalent bond , stereochemistry , substituent , simple (philosophy) , catalysis , combinatorial chemistry , organic chemistry , geography , philosophy , archaeology , epistemology , polymer
Achieving selective C−H activation at a single and strategic site in the presence of multiple C−H bonds can provide a powerful and generally useful retrosynthetic disconnection. In this context, a directing group serves as a compass to guide the transition metal to C−H bonds by using distance and geometry as powerful recognition parameters to distinguish between proximal and distal C−H bonds. However, the installation and removal of directing groups is a practical drawback. To improve the utility of this approach, one can seek solutions in three directions: 1) Simplifying the directing group, 2) using common functional groups or protecting groups as directing groups, and 3) attaching the directing group to substrates via a transient covalent bond to render the directing group catalytic. This Review describes the rational development of an extremely simple and yet broadly applicable directing group for Pd II , Rh III , and Ru II catalysts, namely the N‐methoxy amide (CONHOMe) moiety. Through collective efforts in the community, a wide range of C−H activation transformations using this type of simple directing group have been developed.