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Rh(III)-Catalyzed Redox-Neutral C-H Activation/[3 + 2] Annulation of N-Phenoxy Amides with Propargylic Monofluoroalkynes. 2021

Xiuhua Zhong, and Shuang Lin, and Hui Gao, and Fu-Xiaomin Liu, and Zhi Zhou, and Wei Yi
Key Laboratory of Molecular Target & Clinical Pharmacology and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, Guangdong 511436, China.

An efficient and redox-neutral Rh(III)-catalyzed C-H activation/[3 + 2] annulation of N-phenoxy amides with propargylic monofluoroalkynes has been realized to afford 3-alkylidene dihydrobenzofurans with an interesting α-quaternary carbon center. Combined experimental and computational mechanistic studies revealed that a Rh(III)-Rh(V)-Rh(III) catalytic pathway/uncatalyzed intramolecular [H···F] bonding-assisted SN2'-type substitution cascade might be involved in the catalytic cycle, thereby enabling an excellent site-/regioselectivity with broad substrate/functional group compatibility, including the complete retention of the highly strained cyclobutyl structure in the 3-position.

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