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Switchable C−H Alkylation of Aromatic Acids with Maleimides in Water: Carboxyl as a Diverse Directing Group
Author(s) -
Pu Fan,
Liu ZhongWen,
Zhang LinYan,
Fan Juan,
Shi XianYing
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201900444
Subject(s) - chemistry , conjugate , alkyl , alkylation , chemoselectivity , benzoic acid , ruthenium , redox , catalysis , medicinal chemistry , functional group , ligand (biochemistry) , organic chemistry , combinatorial chemistry , mathematical analysis , biochemistry , receptor , mathematics , polymer
Abstract A ruthenium‐catalyzed protocol to access conjugate addition or decarboxylative conjugate addition of aromatic acids with maleimides has been developed. The reaction shows interesting chemoselectivity with different substituted benzoic acids. The reaction pathway of C−H alkylation is controlled by the intrinsic property of aromatic acids but not reaction conditions. Under almost the same reaction conditions, carboxyl can act as either a classical directing group or a traceless directing group, thereby generating two kinds of products, i. e., 2‐alkyl substituted benzoic acids and alkyl substituted benzenes. These two reactions proceeded under mild and redox‐neutral conditions in neat water under the atmosphere of air, and could be easily scaled up to grams. The decarboxylative conjugate addition, where carboxyl acts as a traceless directing group, can be realized without the addition of any ligand, silver or copper salt.