Copper-mediated aerobic trifluoromethyltelluration of boronic acids with [Me4N][TeCF3]

Jing-Yan Dong; Hao-Nan Wang; Yan-Qian Xie; Cheng-Pan Zhang

doi:10.1016/j.isci.2022.105566

Copper-mediated aerobic trifluoromethyltelluration of boronic acids with [Me₄N][TeCF₃]

iScience. 2022 Nov 15;25(12):105566. doi: 10.1016/j.isci.2022.105566. eCollection 2022 Dec 22.

Authors

Jing-Yan Dong¹, Hao-Nan Wang¹, Yan-Qian Xie¹, Cheng-Pan Zhang^{1

2}

Affiliations

¹ School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan 430070, China.
² Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Abstract

A copper-mediated trifluoromethyltelluration of arylboronic acids with [Me₄N][TeCF₃] using air as an environmental friendly oxidant is presented. The reaction proceeded smoothly under mild conditions in the presence of Cu(OTf)₂ and bipyridine to provide the corresponding trifluoromethyltellurated products in good yields. Vinylboronic acid and arylboronic acid pinacol ester were also suitable substrates in the conversion but the yields are low. This transformation featured simplicity, good functional group tolerance, and a wide range of substrates, allowing for a convenient access to various TeCF₃-containing molecules, and represented the first Chan-Lam type trifluoromethyltelluration with the highly reactive [Me₄N][TeCF₃] salt.

Keywords: Chemistry; Organic chemistry; Organic synthesis.