Comin’s reagent

CAS 145100-51-2, Cat. No EN300-7394471

Triflation reagent

Comin’s reagent has a special niche as an effective reagent for enol triflation. The title compound is a white bench-stable solid that is soluble in most organic solvents. The regent is used as a triflating reagent for lithium enolates kinetically generated from TrLi and for the quenching of thermodynamically generated enolates. Except for ketones, it is known to react with enolates generated from glyoxylates lactones, and aldehydes. Also, Comins’ reagent can be an effective alcohol and phenol trifling reagent. For example, phenol triflation can be triggered from deprotection of the corresponding triisopropylsilyl phenyl ether under basic conditions with a mixture of CsF, Cs₂CO₃, and Comins’ reagent.

Synonyms: N-(5-Chloro-2-pyridinyl)-1,1,1-trifluoroN-[(trifluoromethyl)sulfonyl]methanesulfonamide; 2-[N,N-bis(trifluoromethylsulfonyl)amino]-5-chloropyridine; N,N-bis(trifluoromethylsulfonyl)-5-chloro-2-pyridinamine; N,N-bis(trifluoromethylsulfonyl)-5-chloro-2-pyridylamine; N-(5-chloro2-pyridyl)triflimide

Selected publication

1. N-(5-Chloro-2-Pyridinyl)-1,1,1-Trifluoro-N-[(Trifluoromethyl)Sulfonyl]Methanesulfonamide.

Pelletier G. Encyclopedia of Reagents for Organic Synthesis 2014, 1–5. DOI: 10.1002/047084289X.rn01658