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Hypervalent Iodine-Mediated Synthesis of Sulfinimidate Esters from Sulfenamides

Xunbo Lu*, Guoling Huang, Jianlin Ye, Muhammad Adnan Bashir, Jianfang Su, Kaiyuan Yang, Fangpeng Liang and Xinyu Xu

*Lingnan Normal University (LNU), 29 Cunjin Road, Zhanjiang, Guangdong 524048, Peoples Republic of China, Email: luxunbofoxmail.com

X. Lu, G. Huang, J. Ye, M. A. Bashir, J. Su, K. Yang, F. Liang, X. Xu, Org. Lett., 2023, 25, 2151-2156.

DOI: 10.1021/acs.orglett.3c00678


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Abstract

Phenyliodonium diacetate mediates an efficient oxidative esterification of sulfenamides to provide sulfinimidate esters and sulfilimines under mild and metal-free conditions in very good yields. The protocol is readily scalable and compatible with a diverse range of substrates and functional groups.


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proposed mechanism



Key Words

sulfinimidate esters, PIDA


ID: J54-Y2023