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Fluorinated Ketones as Trapping Reagents for Visible-Light-Induced Singlet Nucleophilic Carbenes

Daniel L. Priebbenow*, Rowan L. Pilkington, Kyle N. Hearn and Anastasios Polyzos

*School of Chemistry, The University of Melbourne, Parkville 3010, Victoria, Australia, Email: daniel.priebbenowunimelb.edu.au

D. L. Priebbenow, R. L. Pilkington, K. N. Hearn, A. Polyzos, Org. Lett., 2021, 23, 2783-2789.

DOI: 10.1021/acs.orglett.1c00708 (free Supporting Information)


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Abstract

Visible-light-induced singlet nucleophilic carbene intermediates can be trapped by fluorinated ketones via 1,2-carbonyl addition to afford benzoin-type products. This efficient, user-friendly, and scalable process provides fluorinated tertiary alcohol derivatives without exogenous catalysts or additives.

 
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proposed mechanism



Key Words

benzoins, trifluoromethyl carbinols, photochemistry


ID: J54-Y2021