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Alkyltriflones in the Ramberg-Bäcklund Reaction: An Efficient and Modular Synthesis of gem-Difluoroalkenes

Yuuki Maekawa, Masakazu Nambo*, Daisuke Yokogawa and Cathleen M. Crudden*

*Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya, Japan, Email: mnamboitbm.nagoya-u.ac.jp, cruddencchem.queensu.ca

Y. Maekawa, M. Nambo, D. Yokogawa, C. M. Crudden, J. Am. Chem. Soc., 2020, 142, 15667-15672.

DOI: 10.1021/jacs.0c07924 (free Supporting Information)


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Abstract

The Ramberg-Bäcklund reaction of alkyl triflones provides structurally diverse, fully substituted gem-difluoroalkenes that are difficult to prepare by treatment with specific Grignard reagents. The Grignard reagent serves both as a base to remove the α-proton and as a Lewis acid to assist C-F bond activation.


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Key Words

Ramberg-Bäcklund Reaction, Fluoroalkenes


ID: J48-Y2020