Oxidative Alkylarylation of N-Aryl Bicyclobutyl Amides with C(sp3)–H Feedstocks via C(sp3)–H/C(sp2)–H Functionalization

Jing Yuan; Jiao Zhou; Peng-Fei Xia; Yu Liu; Ke-Wen Tang; Jian-Hong Fan

doi:10.1002/cjoc.202400748

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (24) : 3399 -3404. DOI: 10.1002/cjoc.202400748

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Oxidative Alkylarylation of N-Aryl Bicyclobutyl Amides with C(sp³)–H Feedstocks via C(sp³)–H/C(sp²)–H Functionalization

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Abstract

Comprehensive Summary:The difunctionalization of bicyclo[1.1.0]butanes is an under-explored transformation that accesses to moieties that are otherwise difficult to prepare. Herein, a new oxidative radical alkylarylation of N-aryl bicyclobutyl amides with C(sp ³)–H feedstocks is achieved in an atom-economic and photocatalyst- and light-free manner. This protocol follows a sequential C(sp ³)–H/C(sp ²)–H functionalization, providing an efficient route for diversity-oriented synthesis of functionalized 3-spirocyclobutyl oxindoles. In particular, a wide range of C(sp ³)–H feedstocks, including ether, alcohol, amine, thioether, polychlorinated methane, silane, acetone, acetonitrile, toluene, and alkane are all suitable for the C(sp ³)–H functionalization, demonstrating the broad applicability of this transformation.

Keywords

Bicyclo[1.1.0]butanes / C–H Functionalization / Strain-release Difunctionalization / Spirocyclic oxindoles / Cyclization / Alkylation / Radical reactions / C(sp ³)–H Feedstocks

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Jing Yuan, Jiao Zhou, Peng-Fei Xia, Yu Liu, Ke-Wen Tang, Jian-Hong Fan. Oxidative Alkylarylation of N-Aryl Bicyclobutyl Amides with C(sp³)–H Feedstocks via C(sp³)–H/C(sp²)–H Functionalization. Chinese Journal of Chemistry, 2024, 42(24): 3399-3404 DOI:10.1002/cjoc.202400748