Enantioselective C(sp 3 )-H Functionalization of Oxacycles via Photo-HAT/Nickel Dual Catalysis.

Sheng Xu,Yuanyuan Ping,Wei Li, Haoyun Guo, Yinyan Su,Ziyang Li,Minyan Wang,Wangqing Kong

Journal of the American Chemical Society(2023)

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The selective functionalization of ubiquitous but inert C-H bonds is highly appealing in synthetic chemistry, but the direct transformation of hydrocarbons lacking directing groups into high-value chiral molecules remains a formidable challenge. Herein, we develop an enantioselective C(sp)-H functionalization of undirected oxacycles via photo-HAT/nickel dual catalysis. This protocol provides a practical platform for the rapid construction of high-value and enantiomerically enriched oxacycles directly from simple and abundant hydrocarbon feedstocks. The synthetic utility of this strategy is further demonstrated in the late-stage functionalization of natural products and the synthesis of many pharmaceutically relevant molecules. Experimental and density functional theory calculation studies provide detailed insights into the mechanism and the origin of enantioselectivity for the asymmetric C(sp)-H functionalization.
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