合成化学2024,Vol.32Issue(7) :643-648.DOI:10.15952/j.cnki.cjsc.1005-1511.23097

二氯亚砜活化的芳基肼自身偶联反应

Thionyl Chloride-activated Homo-coupling Reaction of Aryl Hydrazine

杜剑雄 钟品勇 刘晋彪
合成化学2024,Vol.32Issue(7) :643-648.DOI:10.15952/j.cnki.cjsc.1005-1511.23097

二氯亚砜活化的芳基肼自身偶联反应

Thionyl Chloride-activated Homo-coupling Reaction of Aryl Hydrazine

杜剑雄 1钟品勇 1刘晋彪1
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作者信息

  • 1. 江西理工大学 材料冶金化学学部江西省功能分子材料化学重点实验室,江西赣州 341000
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摘要

联芳烃作为一类重要的芳香化合物,广泛应用于医药、材料和化工等领域,发展新颖简单的Aryl—Aryl合成方法具有重要意义.本文以芳基肼盐酸盐为原料,通过筛选不同的碱、溶剂和活化剂的用量,优化了较佳的实验条件:以4-二甲氨基吡啶为促进剂,乙腈为溶剂,1.5 eq的二氯亚砜为活化剂,在5 min内以24%~68%的产率合成了 11个联苯衍生物,目标化合物结构经1H NMR和13C NMR确证.该方法具有反应条件温和,无需过渡金属催化等特点.

Abstract

As a class of important aromatic compounds,biaryl hydrocarbons are widely used in the fields of medicine,materials,and chemistry.It is significant to develop novel and simple methods for synthesizing aryl-aryl compounds.In this paper,aryl hydrazine hydrochloride was used as the raw ma-terial.By screening different amounts of bases,solvents,and activators,an optimal experimental con-dition was optimized:4-dimethylaminopyridine as the promoter,acetonitrile as the solvent,1.5 equiv-alents of dichlorosulfoxide as the activator.Under these conditions,11 biphenyl derivatives were syn-thesized in 5 minutes with yields ranging from 24%~68%.The target compounds were confirmed by 1H NMR and 13 C NMR.This method has the advantages of mild reaction conditions and no need for transition metal catalysis.

关键词

芳基肼/偶联反应/二氯亚砜/4-二甲氨基吡啶/无金属催化

Key words

aryl hydrazine/coupling reaction/thionyl chloride/4-dimethylaminopyridine/metal-free catalysis

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基金项目

国家自然科学基金资助项目(21961014)

出版年

2024
合成化学
四川省化学化工学会 中国科学院成都有机化学研究所

合成化学

CSTPCD
影响因子:0.42
ISSN:1005-1511
参考文献量2
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