TMSCF<sub>2</sub>Br‐Enabled Fluorination–Aminocarbonylation of Aldehydes: Modular Access to α‐Fluoroamides
An Liu, Chuanfa Ni, Qiqiang Xie, Jinbo Hu
Abstract
Abstract A protocol for the modular assembly of the α‐fluoroamide motif has been developed, which provides a practical method for the efficient synthesis of structurally diverse α‐fluoroamides from easily available aldehydes and tertiary amines through a three‐component fluorination–aminocarbonylation process. The key to the success of this process is taking advantage of the multiple roles of the unique difluorocarbene reagent TMSCF 2 Br (TMS=trimethylsilyl). The mechanism of the process involves the 1,2‐fluorine and oxygen migrations of the in situ formed TMS‐protected α‐aminodifluoromethyl carbinol intermediates, which represents a new type of deoxyfluorination reaction.
Topics & Concepts
DifluorocarbeneReagentModular designTrimethylsilylCombinatorial chemistryFluorineChemistryComputer scienceOrganic chemistryProgramming languageFluorine in Organic ChemistryCyclopropane Reaction MechanismsCarbon dioxide utilization in catalysis