Chemistry - An Asian Journal 2018-04-10

Sulfinate‐Salt‐Mediated Radical Relay Cyclization of Cyclic Ethers with 2‐Alkynylbenzonitriles toward 3‐Alkylated 1‐Indenones

Xiao‐Tong Zhu; Tian‐Shu Zhang; Qi Zhao; Pei‐Jun Cai; Wen‐Juan Hao; Shu‐Jiang Tu; Bo Jiang

Index: 10.1002/asia.201800211

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Abstract

10.1002/asia.201800211 picture

A new sulfinate salt‐mediated radical relay for the completion of C(sp3)−H bond indenylation of cyclic ethers with readily available 2‐alkynylbenzonitriles by combining silver/tert‐butyl peroxide (TBHP) was established, providing a wide range of 3‐alkylated 1‐indenones with generally good yields. Interestingly, the current reaction system can tolerate an S‐centered radical and a C‐centered radical in one pot, in which the S‐centered radical promotes the formation of the C‐centered radical to induce a radical cascade without disturbing the reaction process. A reaction mechanism is also proposed based on control experiments.