An Electrophilic Approach to the Palladium-Catalyzed Carbonylative C-H Functionalization of Heterocycles

Journal of the American Chemical Society
Jevgenijs Tjutrins, Bruce A Arndtsen

Abstract

A palladium-catalyzed approach to intermolecular carbonylative C-H functionalization is described. This transformation is mediated by P(t)Bu3-coordinated palladium catalyst and allows the derivatization of a diverse range of heterocycles, including pyrroles, indoles, imidazoles, benzoxazoles, and furans. Preliminary studies suggest that this reaction may proceed via the catalytic formation of highly electrophilic intermediates. Overall, this provides with an atom-economical and general synthetic route to generate aryl-(hetero)aryl ketones using stable reagents (aryl iodides and CO) and without the typical need to exploit pre-metalated heterocycles in carbonylative coupling chemistry.

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Citations

Feb 9, 2017·The Journal of Organic Chemistry·Yu BaiMingji Dai
Apr 14, 2017·The Journal of Organic Chemistry·Yongliang TuJunfeng Zhao
Jun 13, 2017·Chemical Communications : Chem Comm·Lijun LuAiwen Lei
Nov 15, 2017·Organic & Biomolecular Chemistry·Min LiuShuang-Feng Yin
Jun 21, 2018·Natural Product Reports·Kaiqing MaMingji Dai
Apr 4, 2019·Chemistry : a European Journal·Yohei OgiwaraNorio Sakai
Feb 8, 2020·Organic & Biomolecular Chemistry·Attoor Chandrasekhar, Sethuraman Sankararaman
Aug 7, 2018·Journal of the American Chemical Society·Maximiliano De La Higuera Macias, Bruce A Arndtsen

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