Nucleophilic Substitution of Tertiary Sulfonamides: Construction of Sulfonate Esters
Xiangshuai Du, Guodan Lu, Tao Zhang, Congzhou Wang, Yong Wang（王勇）*,Xiaobing Wan（万小兵）*
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123,China
Org. Lett.2025, 27, 2268−2273
Abstract: Under the combined action of trichloroisocyanuric acid (TCCA) and triflic acid (TfOH), tertiary sulfonamides are efficiently activated, leading to the in situ generation of electrophilic sulfonamide salts. These electrophilic salts subsequently undergo nucleophilic substitution by alcohols, resulting in the formation of sulfonate esters under mild conditions. Other advantages of this method include the absence of transition-metal catalysts, broad substrate applicability, and high functional-group tolerance.
Article information: //doi.org/10.1021/acs.orglett.5c00587
