Double C–N bond cleavages of <i>N</i>-alkyl 4-oxopiperidinium salts: access to unsymmetrical tertiary sulfonamides
作者:Ying Fu、Ming-Peng Li、Chun-Zhao Shi、Fang-Rong Li、Zhengyin Du、Congde Huo
DOI:10.1039/c9ob02107h
日期:——
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
在本文中,提出了N-烷基4-氧代哌啶鎓盐的区域特异性双环内C–N键裂解。反应顺序包括一个电荷转移络合物,原位磺酰氯和之间形成Ñ甲基吗啉,磺酰氯,其诱导S-Cl键均裂,产生反应性基团磺酰进一步诱导的双C-N键断裂ñ -烷基4-氧代哌啶鎓盐。如此产生的仲胺被磺酰氯捕获,得到所需的磺酰胺产物。该协议的关键特征是,在无金属和无氧化剂的条件下,一步切割了4-氧杂环哌啶环的两个环内C–N键。