Copper-catalyzed radical trifluoromethylalkynylation of unactivated alkenes with terminal alkynes

• Published in: Journal of fluorine chemistry Vol. 267; pp. 110107 - 110112
• Main Authors: Ren, Yang-Qing, Yang, Chang-Jiang, Li, Zhong-Liang, Gu, Qiang-Shuai, Liu, Lin, Liu, Xin-Yuan
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.04.2023; Elsevier
• Subjects: Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Copper; Physical Sciences; Radical reaction; Science & Technology; Terminal alkyne; Trifluoromethylalkynylation; Unactivated alkenes; Unactivated alkenes; Terminal alkyne; Radical reaction; Trifluoromethylalkynylation; Copper; STYRENES; SILVER; ELIMINATION; 1,2-ADDITION; ALKYNYLATION; BROMIDES; C-H BONDS; IODIDES; FLUORINE; 1,2-DIFUNCTIONALIZATION
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2023.110107

•Terminal alkynes are used in trifluoromethylalkynylation of unactivated alkenes.•The design of copper/N,N,N-ligand catalyst ensures its success.•Mild conditions make it operationally simple. A copper-catalyzed three-component radical trifluoromethylalkynylation of unactivated alkenes is realized from Togni-II reagent and readily available terminal alkynes under mild conditions to afford an array of β-trifluoromethylated alkynes. The utilization of a multidentate N,N,N-ligand is crucial for the efficient radical generation and the C(sp3)–C(sp) bond formation. Facile transformations of the difunctionalization products highlight its potential utility in the synthesis of various trifluoromethyl-containing building blocks. [Display omitted]