Palladium/Norbornene-Catalyzed Decarbonylative Difunctionalization of Thioesters
journal contributionposted on 2021-10-15, 17:21 authored by Ming-Liang Han, Jun-Jie Chen, Hui Xu, Zhi-Cong Huang, Wei Huang, Yu-Wen Liu, Xing Wang, Min Liu, Zi-Qiong Guo, Hui-Xiong Dai
The transition-metal-catalyzed decarboxylation of aryl carboxylic acids has drawn significant attention as an efficient and practical tool for the synthesis of substituted arenes. However, the decarboxylative construction of polysubstituted arenes with different contiguous substituents has not been widely reported. Herein, we describe a novel decarbonylative Catellani reaction via palladium-catalyzed, norbornene (NBE)-mediated polyfunctionalization of aromatic thioesters, which serve as readily available carboxylic acid derivatives. A variety of alkenyl, alkyl, aryl, and sulfur moieties could be conveniently introduced into the ipso-positions of the aromatic thioesters. By combining carboxyl-directed C–H functionalization and the classical Catellani reaction, our protocol allows for the construction of 1,2,3-trisubstituted and 1,2,3,4-tetrasubstituted arenes from simple aromatic acids. Furthermore, the late-stage functionalization of a series of drug molecules highlights the potential utility of the reaction.
sulfur moieties coulddrug molecules highlightsdrawn significant attentiondifferent contiguous substituentssimple aromatic acidsclassical catellani reactioncatalyzed decarbonylative difunctionalizationaryl carboxylic acidswidely reportedtetrasubstituted arenessubstituted arenesstage functionalizationprotocol allowspractical toolpotential utilitypolysubstituted arenesipso conveniently introducedcombining carboxylcatalyzed decarboxylationaromatic thioesters>- positions