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有机化学
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有机化学 ›› 2014, Vol. 34 ›› Issue (4): 767-773.DOI: 10.6023/cjoc201308011 上一篇    下一篇

研究论文

醋酸铜促进的芳基磺酰肼自身偶联合成二芳基砜

王建伟, 韦珊红, 赵保丽, 程凯   

  1. 绍兴文理学院 浙江省精细化学品传统工艺替代技术研究重点实验室 绍兴 312000
  • 收稿日期:2013-08-09 修回日期:2013-10-11 发布日期:2013-12-14
  • 通讯作者: 程凯 E-mail:chengkai@usx.edu.cn
  • 基金资助:

    国家自然科学基金（No. 21202102）、浙江省自然科学基金（No. LQ14B020001）、浙江省科技厅（No. 2012R10014-15）、浙江省教育厅（No. Y201328443）和绍兴市科技计划（No. 2013014017）资助项目.

Cu(OAc)2 Mediated Homo-coupling with Arylsulfonyl Hydrazides to Synthesize Biarylsulfone

Wang Jianwei, Wei Shanhong, Zhao Baoli, Cheng Kai   

  1. Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000
  • Received:2013-08-09 Revised:2013-10-11 Published:2013-12-14
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21202102), the Zhejiang Provincial Natural Science Foundation of China (No. LQ14B020001), the Science Technology Department of Zhejiang Province (No. 2012R10014-15), the Education Department of Zhejiang Province (No. Y201328443) and the Science Technology Project of Shaoxing City (No. 2013014017).

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研究了一种新颖的醋酸铜促进的芳基磺酰肼的自身偶联反应. 该反应通过分子间脱硫和脱氮的过程，高选择性高产率的合成对称的二芳基砜类化合物. 该反应中溶剂对反应的副产物的产生有十分显著的影响. 反应无需惰性气体保护，具有良好的官能团耐受性，硝基、卤素等官能团及杂环体系都对反应无明显影响. 该合成方法可以用于治疗麻风病的药物氨苯砜的制备.

关键词: 自身偶联, 二芳基砜合成, 芳基磺酰肼

A new homocoupling pattern with arylsulfonyl hydrazides promoted by Cu(OAc)2 is described. This transformation is proceeded via intermolecular denitrification and desulfitation. Symmetrical diaryl sulfone derivatives were obtained with high selectivity and reactivity. The solvents showed striking influence to the formation of distinctive by-products. The reported homocoupling reactions are very practical as it does not require the protection of inert gas and tolerant to the many functional groups, especially nitro, halogen and heterocyclic system. The synthetic method has been applied to the synthesis of dapsone.

Key words: homocoupling, biarylsulfone synthesis, arylsulfonyl hydrazides