Beckman Scholars Chris AmEnde ('02), Nicholas Ball ('03) & Cristian Woroch ('18) brought together Pomona College and Pfizer to introduce a new method toward sulfonamides from sulfonyl fluorides using a calcium salt. The rare collaboration between a small liberal arts college and industry resulted in the first method to use a single set of reaction conditions for the transformation - and may highlight the sulfonyl fluoride as a useful precursor to sulfonylation reactions.
A method using calcium triﬂimide [Ca(NTf2)2] as a Lewis acid to activate sulfonyl ﬂuorides toward nucleophilic addition with amines is described. The reaction
converts a wide array of sterically and electronically diverse sulfonyl ﬂuorides and amines into the corresponding sulfonamides in good yield.
Organic Letters, 2018
Sulfonamide Synthesis via Calcium Triﬂimide Activation of Sulfonyl Fluorides