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

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.

Automated summary

Utilization of singlet nucleophilic carbenes (SNCs) with only one heteroatom donor in chemical synthesis remains underutilized. Recent discovery shows that visible-light-induced SNC intermediates can react with fluorinated ketones to afford benzoin-type products, providing an efficient, user-friendly, and scalable process for accessing fluorinated tertiary alcohol derivatives without the use of exogenous catalysts or additives.