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Organocatalytic C?H Functionalization of Simple Alkanes
Authors:Fen Su  Fengfei Lu  Kun Tang  Xiaokang Lv  Zhongfu Luo  Fengrui Che  Hongyan Long  Prof Xingxing Wu  Prof?Dr Yonggui Robin Chi
Institution:1. National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang, 550025 China

These authors contributed equally to this work.;2. National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang, 550025 China

Abstract:The direct functionalization of inert C(sp3)-H bonds to form carbon-carbon and carbon-heteroatom bonds offers vast potential for chemical synthesis and therefore receives increasing attention. At present, most successes come from strategies using metal catalysts/reagents or photo/electrochemical processes. The use of organocatalysis for this purpose remains scarce, especially when dealing with challenging C?H bonds such as those from simple alkanes. Here we disclose the first organocatalytic direct functionalization/acylation of inert C(sp3)-H bonds of completely unfunctionalized alkanes. Our approach involves N-heterocyclic carbene catalyst-mediated carbonyl radical intermediate generation and coupling with simple alkanes (through the corresponding alkyl radical intermediates generated via a hydrogen atom transfer process). Unreactive C?H bonds are widely present in fossil fuel feedstocks, commercially important organic polymers, and complex molecules such as natural products. Our present study shall inspire a new avenue for quick functionalization of these molecules under the light- and metal-free catalytic conditions.
Keywords:Aryl Radical  C?H Functionalization  Hydrogen Atom Transfer  N-Heterocyclic Carbene  Organocatalysis
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