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Fluorinated Ketones as Trapping Reagents for Visible-Light-Induced Singlet Nucleophilic Carbenes
Daniel L Priebbenow1, Rowan L Pilkington1, Kyle N Hearn2
1School of Chemistry, The University of Melbourne, Parkville 3010, Victoria, Australia.
Abstract:
Singlet nucleophilic carbenes (SNCs) containing only one heteroatom donor remain underutilized in chemical synthesis. We recently discovered that visible-light-induced SNC intermediates can be trapped by fluorinated ketones via 1,2-carbonyl addition to afford benzoin-type products. This discovery represents a rare example of nucleophilic carbenes reacting with ketones and delivers an efficient, user-friendly, and scalable process for accessing fluorinated tertiary alcohol derivatives driven only by light circumventing the use of exogenous catalysts or additives.
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