Stereoselective synthesis of fluoroalkylated (Z)-alkene via nickel-catalyzed and iron-mediated hydrofluoroalkylation of alkynes

• Published in: ORGANIC CHEMISTRY FRONTIERS Vol. 8; no. 22; pp. 6377 - 6383
• Main Authors: Li, Xiang-Rui, Li, Wen-Xin, Zhang, Zhuo-Wen, Shen, Chuanji, Zhou, Xiaocong, Chu, Xue-Qiang, Rao, Weidong, Shen, Zhi-Liang
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 09.11.2021; Royal Society of Chemistry
• Subjects: Alkenes; Alkynes; Chemistry; Chemistry, Organic; Functional groups; Iodides; Iron; Nickel; Organic chemistry; Perfluoroalkyl & polyfluoroalkyl substances; Physical Sciences; Science & Technology; Stereoselectivity; Substrates; Sugar; POLYFLUOROALKYL KETONES; ALPHA,BETA-UNSATURATED CARBOXYLIC-ACIDS; INTRAMOLECULAR CYCLIZATION; SELECTIVE DIFLUOROALKYLATION; COUPLING REACTION; DIRECT INSERTION; TRANSFER RADICAL-ADDITION; DECARBOXYLATIVE DIFLUOROALKYLATION; GEM-DIFLUOROMETHYLENATION; UNACTIVATED ALKENES
• ISSN: 2052-4129; 2052-4110; 2052-4110
• DOI: 10.1039/d1qo00983d

An efficient nickel-catalyzed, iron-mediated hydrofluoroalkylation of alkynes with bromodifluoroacetate or perfluoroalkyl iodide was developed. The reactions proceeded efficiently via a radical reaction pathway to give fluoroalkylated (Z)-alkenes in moderate to good yields with good control of stereoselectivity (up to 99 : 1 Z/E), exhibiting both wide substrate scope and broad functional group tolerance. In addition, the method also entailed the easy functionalization of alkyne-tethered complex molecules derived from sugars and pharmaceuticals.