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Carboxylic Acids as Directing Groups for C−H Bond Functionalization
Author(s) -
Pichette Drapeau Martin,
Gooßen Lukas J.
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.201603263
Subject(s) - carboxylate , surface modification , chemistry , regioselectivity , halogen , combinatorial chemistry , group (periodic table) , halogenation , halogen bond , stereochemistry , catalysis , organic chemistry , alkyl
The selective transformation of C−H bonds is one of the most desirable approaches to creating complexity from simple building blocks. Several directing groups are efficient in controlling the regioselectivity of catalytic C−H bond functionalizations. Among them, carboxylic acids are particularly advantageous, since they are widely available in great structural diversity and at low cost. The carboxylate directing groups can be tracelessly cleaved or may serve as the anchor point for further functionalization through decarboxylative couplings. This Minireview summarizes the substantial progress made in the last few years in the development of reactions in which carboxylate groups direct C−H bond functionalizations with formation of C−C, C−O, C−N, or C−halogen bonds at specific positions. It is divided into sections on C−C, C−O, C−N, and C−halogen bond formation, each of which is subdivided by reactions and product classes. Particular emphasis is placed on methods that enable multiple derivatizations by combining carboxylate‐directed C−H functionalization with decarboxylative couplings.