Visible-Light Induced Singlet Nucleophilic Carbenes: Rapid and Mild Access to Fluorinated Tertiary Alcohol Derivatives

21 December 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Singlet nucleophilic carbenes (SNCs) that contain only one heteroatom donor remain underexplored and underutilized in chemical synthesis. To discover new synthetic strategies that harness these SNCs as reactive intermediates, aromatic or aliphatic siloxy carbenes represent excellent model substrates as they can be readily generated photochemically from stable acyl silane precursors. We herein report the discovery that photochemically generated siloxy carbenes undergo 1,2-carbonyl addition to trifluoromethyl ketones, followed by a silyl transfer process to afford benzoin-type products. This new transformation is a rare example of the use of ketones as trapping reagents for SNC intermediates and delivers an efficient, user-friendly and scalable process to access fluorinated tertiary alcohol derivatives driven by only light, circumventing the use of catalysts or additives.



Supplementary materials

Visible Light Induced SNCs - Supporting Information


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