Fluorinated Ketones as Trapping Reagents for Visible-Light-Induced Singlet Nucleophilic Carbenes
Daniel L. Priebbenow, Rowan L. Pilkington, Kyle N. Hearn, Anastasios Polyzos
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.
Topics & Concepts
ChemistryNucleophileUmpolungBenzoinNucleophilic additionReagentSinglet statePhotochemistryHeteroatomCatalysisCombinatorial chemistryAlcoholVisible spectrumOrganic chemistryAlkylPhysicsNuclear physicsOptoelectronicsExcited stateFluorine in Organic ChemistryN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCyclopropane Reaction Mechanisms