Transition-Metal-Free Synthesis of Aryl Trifluoromethyl Thioethers through Indirect Trifluoromethylthiolation of Sodium Arylsulfinate with TMSCF3

Changge Zheng; Chao Jiang; Shuai Huang; Kui Zhao; Yingying Fu; Mingyu Ma; Jianquan Hong

doi:10.1021/acs.orglett.1c02656

Transition-Metal-Free Synthesis of Aryl Trifluoromethyl Thioethers through Indirect Trifluoromethylthiolation of Sodium Arylsulfinate with TMSCF₃

Org Lett. 2021 Sep 3;23(17):6982-6986. doi: 10.1021/acs.orglett.1c02656. Epub 2021 Aug 17.

Authors

Changge Zheng^{1

2}, Chao Jiang¹, Shuai Huang¹, Kui Zhao¹, Yingying Fu¹, Mingyu Ma¹, Jianquan Hong¹

Affiliations

¹ Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu 214122, P. R. China.
² School of Chemical Engineering, Xinjiang Agricultural University, Urumqi 830052, Xinjiang Uygur Autonomous Region, P. R. China.

PMID: 34474573
DOI: 10.1021/acs.orglett.1c02656

Abstract

Herein, we report an indirect trifluoromethylthiolation of sodium arylsulfinates. This transition-metal-free reaction significantly provides an environmentally friendly and practical synthetic method for aryl trifluoromethyl thioethers using commercial Ruppert-Prakash reagent TMSCF₃. This approach is also a potential alternative to the current industrial production method owing to facile substrates, excellent functional group compatibility, and operational simplicity.