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N-Heterocyclic Carbene-Catalyzed Radical Relay Enabling Vicinal Alkylacylation of Alkenes

Takuya Ishii, Kenji Ota, Kazunori Nagao* and Hirohisa Ohmiya*

*Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan, Email: nkazunorip.kanazawa-u.ac.jp, ohmiyap.kanazawa-u.ac.jp

T. Ishii, K. Ota, K. Nagao, H. Ohmiya, J. Am. Chem. Soc., 2019, 141, 14073-14077.

DOI: 10.1021/jacs.9b07194 (free Supporting Information)



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Abstract

A N-heterocyclic carbene-catalyzed radical relay enables the vicinal alkylacylation of styrenes, acrylates and acrylonitrile with complete regioselectivity using aldehydes and tertiary alkyl carboxylic acid-derived redox-active esters  to produce functionalized ketone derivatives.

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Key Words

acylation, alkylation, multicomponent reactions, organocatalysis


ID: J48-Y2019