Copper-Catalyzed Ring-Opening Defluoroborylation of gem-Difluorinated Cyclobutenes: A General Route to Bifunctional 1,3-Dienes and Their Applications
2022
Jia, Jie | Yuan, Fushan | Zhang, Zihao | Song, Xuejiao | Hu, Fangdong | Xia, Ying
The exploration of the reactivity of gem-difluorinated small-size rings has continuously drawn attention in recent years but is limited to three-membered carbocycles. Herein we report a copper-catalyzed reaction of gem-fluorinated cyclobutenes with bis(pinacolato)diboron (B₂pin₂). A sequence of defluoroborylation and a ring-opening process produces B,F-bifunctional 1,3-dienes in a stereoselective manner. The transformation together with the efficient downstream coupling of the boronate and the fluoride moieties collectively constitutes a modular route to highly functionalized and stereocontrolled 1,3-dienes.
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