吸电子基取代的N-芳基磺酰腙作为重氮化合物前体的研究进展

Research Progress on EWG-Substituted N-Arylsulfonylhydrazones as the Diazo Compound Precursor

N-芳基磺酰腙是一类稳定的重氮化合物替代物,其中,N-对甲基苯磺酰腙研究历史悠久,在卡宾化学中占据重要地位,相关的研究报道及综述较多.近年来,作为一类更加温和的重氮替代物,吸电子基取代的N-芳基磺酰腙参与的化学反应发展迅速,但是相关的研究梳理工作相对缺乏.因此,本综述聚焦于吸电子基取代的N-芳基磺酰腙作为重氮化合物替代物在有机合成反应中的研究进展,重点总结了N-邻硝基苯磺酰腙和N-邻三氟甲基苯磺酰腙参与的偶联、环化、插入、多组分反应和Doyle-Kirmse等反应.

N-arylsulfonyl hydrazones were a kind of stable diazo surrogates in organic synthesis. Among them, N-tosylhydrazones occupied main position in the research of carbene chemistry, and many reactions involving N-tosylhydrazones and reviews were published. In recent years, the chemical reactions involving electron-withdrawing groups(EWG)-substituted N-arylsulfonylhydrazones as milder diazo surrogates have been developed rapidly. However, these reactions were not summarized. Therefore, this review focuses on the research progress on EWG-substituted N-arylsulfonylhydrazones used as diazo surrogates in organic synthesis reactions, and emphasized the coupling, cyclization, insertion, multicomponent and Doyle-Kirmse reaction involved N-o-nitrobenzenesulfonylhydrazides and N-o-triftosylhydrazones.