The Reaction of Aryl Thiols or Thioureas with o‐Diiodoarenes/NaH to Access o‐Iodoaryl Thioethers

Author:

Hu Min12,Liu Dianfan12,Liu Yuan1,Luo Fan3,Chen Xiaobei4,Yin Yuejia1,Zhang Shilei12ORCID,Hu Yanwei12

Affiliation:

1. Jiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences Soochow University 199 Ren'ai Road Suzhou Jiangsu 215123 People's Republic of China

2. Jiangsu Province Engineering Research Center of Precision Diagnostics and Therapeutics Development Soochow University Suzhou 215123 People's Republic of China

3. College of Medicine Jiaxing University 118 Jiahang Road Jiaxing 314001 People's Republic of China

4. State Key Laboratory of Bioreactor Engineering Shanghai Key Laboratory of New Drug Design School of Pharmacy East China University of Science & Technology Shanghai 200237 People's Republic of China

Abstract

AbstractHerein we report a method for the synthesis of thioethers by forging C(aryl)‐S bond via an aryne mechanism. The active aryne species can be generated from o‐diiodoarenes and NaH in THF at room temperature, then lead to the arylations of a wide range of aryl thiols and thioureas. Different from transition metal‐catalyzed cross‐coupling reactions, no disubstituted byproduct is formed in our protocol. The o‐iodoaryl thioether products are intermediates that could be transformed into pharmaceutically interesting molecules.

Funder

National Natural Science Foundation of China

Publisher

Wiley

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