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39.1.4.1.4 Method 4: Synthesis from Sulfonamides

DOI: 10.1055/sos-SD-039-00002

Drabowicz, J.; Kiełbasiński, P.; Łyżwa, P.; Zając, A.; Mikołajczyk, M.Science of Synthesis, (20083952.

Sulfonamides react with alcohols in the presence of acidic catalysts to form the corresponding sulfonates (see reviews in HoubenWeyl, Vol. E 11, p 1093 and elsewhere[‌8‌]). Of particular importance are the bis(trifluoromethylsulfonyl)imides that serve as a source of the trifluoromethylsulfonyl unit.[‌9‌] For example, 2-[N,N-bis(trifluoromethylsulfonyl)amino]-5-chloropyridine, the Comins reagent, is a convenient alternative to trifluoromethanesulfonic anhydride and, among others, is used for the synthesis of alkenyl trifluoromethanesulfonates from the enolates of carbonyl compounds. A specific example, uses 3,4-dihydro-2(3H)-thiophenone as the starting material en route to 4,5-dihydro-2-thienyl trifluoromethanesulfonate (108) (Scheme 83).[‌233‌‌235‌] N,N-Bis(trifluoromethylsulfonyl)aniline (N-phenyltriflimide) is also effective in similar transformations (Scheme 83).[‌234‌,‌236‌‌238‌]

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