Synthesis of Indole-Substituted Trifluoromethyl Sulfonium Ylides by Cp*Rh(III)-Catalyzed Diazo-carbenoid Addition to Trifluoromethylthioether

Shao-Yong Chen; Yi-Chuan Zheng; Xu-Ge Liu; Jia-Lin Song; Lin Xiao; Shang-Shi Zhang

doi:10.1021/acs.joc.3c00060

Synthesis of Indole-Substituted Trifluoromethyl Sulfonium Ylides by Cp*Rh(III)-Catalyzed Diazo-carbenoid Addition to Trifluoromethylthioether

J Org Chem. 2023 May 5;88(9):5512-5519. doi: 10.1021/acs.joc.3c00060. Epub 2023 Apr 3.

Authors

Shao-Yong Chen¹, Yi-Chuan Zheng¹, Xu-Ge Liu², Jia-Lin Song¹, Lin Xiao¹, Shang-Shi Zhang¹

Affiliations

¹ Center for Drug Research and Development, Guangdong Provincial Key Laboratory of Advanced Drug Delivery, Guangdong Provincial Engineering Center of Topical Precise Drug Delivery System, Guangdong Pharmaceutical University, Guangzhou, 510006, P. R. China.
² School of Pharmacy, Henan University, Kaifeng, Henan 475004, China.

PMID: 37011236
DOI: 10.1021/acs.joc.3c00060

Abstract

The indole-substituted trifluoromethyl sulfonium ylide has been developed via Cp*Rh(III)-catalyzed diazo-carbenoid addition to trifluoromethylthioether and is the first example of an Rh(III)-catalyzed diazo-carbenoid addition reaction with trifluoromethylthioether. Several kinds of indole-substituted trifluoromethyl sulfonium ylide were constructed under mild reaction conditions. The reported method exhibited high functional group compatibility and broad substrate scope. In addition, the protocol was found to be complementary to the method disclosed by a Rh(II) catalyst.