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Rh(III)-Catalyzed C-H Activation/[3 + 2] Annulation of N-Phenoxyacetamides via Carbooxygenation of 1,3-Dienes

Liexin Wu, Liping Li, Haiman Zhang, Hui Gao, Zhi Zhou* and Wei Yi*

*The Fifth Affiliated Hospital, School of Pharmaceutical Sciences, Guangzhou Medical University, Guangzhou, Guangdong 511436, China, Email: zhouzhigzhmu.edu.cn, yiweigzhmu.edu.cn

L. Wu, L. Li, H. Zhang, H. Gao, Z. Zhou, W. Yi, Org. Lett., 2021, 23, 3844-3849.

DOI: 10.1021/acs.orglett.1c00945 (free Supporting Information)


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Abstract

A unique Rh(III)-catalyzed C-H activation of N-phenoxyacetamides followed by carbooxygenation of 1,3-dienes enables the construction of dihydrobenzofurans. This redox-neutral [3 + 2] annulation offers chemoselectivity, good substrate/functional group compatibility, and profound synthetic potentials. An asymmetric approach has also been demonstrated.

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proposed mechanism



Key Words

2,3-Dihydrobenzofurans


ID: J54-Y2021