文献类型：期刊文献

英文题名：Double C-N bond cleavages of N-alkyl 4-oxopiperidinium salts: access to unsymmetrical tertiary sulfonamides

作者：Fu, Ying[1];Li, Ming-Peng[1];Shi, Chun-Zhao[1];Li, Fang-Rong[2];Du, Zhengyin[1];Huo, Congde[1]

第一作者：Fu, Ying

通信作者：Fu, Y[1];Du, ZY[1];Huo, CD[1]

机构：[1]Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Gansu, Peoples R China;[2]Gansu Univ Tradit Chinese Med, Pharm Dept, Lanzhou 743000, Gansu, Peoples R China

第一机构：Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Gansu, Peoples R China

通信机构：[1]corresponding author), Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Gansu, Peoples R China.

年份：2019

卷号：17

期号：48

起止页码：10172

外文期刊名：ORGANIC & BIOMOLECULAR CHEMISTRY

收录：;EI(收录号：20195207903450);Scopus(收录号：2-s2.0-85076387283);WOS:【SCI-EXPANDED(收录号:WOS:000502301500007)，CCR-EXPANDED(收录号:WOS:000502301500007)】；

基金：The authors are grateful for the financial support from the National Natural Science Foundation of China (No. 21762040 & 21762039).

语种：英文

外文关键词：Amides - Amines - Charge transfer - Chlorine compounds - Salts

摘要：In this paper, regiospecific, double intraannular C-N bond cleavages of N-alkyl 4-oxopiperidinium salts are presented. The reaction sequence involves a charge-transfer complex, in situ formed between sulfonyl chloride and N-methylmorpholine, which induces S-Cl bond homolysis of sulfonyl chloride, yielding a reactive sulfonyl radical that further induces the double C-N bond cleavages of N-alkyl 4-oxopiperidinium salt. The secondary amine thus produced was trapped by sulfonyl chloride to yield the desired sulfonamide product. The key feature of this protocol is that two intraannular C-N bonds of the 4-oxopiperidine ring are cleaved in one step under metal- and oxidant-free conditions.