Copper‐Catalyzed Oxidative Cross‐Coupling of Electron‐Deficient Polyfluorophenylboronate Esters with Terminal Alkynes

• Published in: Chemistry : a European journal Vol. 26; no. 71; pp. 17267 - 17274
• Main Authors: Liu, Zhiqiang, Budiman, Yudha P., Tian, Ya‐Ming, Friedrich, Alexandra, Huang, Mingming, Westcott, Stephen A., Radius, Udo, Marder, Todd B.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 18.12.2020; Wiley Subscription Services, Inc; John Wiley and Sons Inc
• Subjects: Alkynes; boronate esters; Chemistry; Chemistry, Multidisciplinary; Copper; coupling reactions; Cross coupling; Esters; fluorine; fluoroarenes; Functional groups; Physical Sciences; Science & Technology; Sonogashira reaction; Substrates; ALKYNYLCOPPER REAGENTS; ORTHO-ETHYNYLATION; BUILDING-BLOCKS; coupling reactions; CRYSTAL-STRUCTURES; ARYLBORONIC ACIDS; C-H ALKYNYLATION; fluoroarenes; QUATERNARY STEREOGENIC CENTERS; boronate esters; PHASE-BEHAVIOR; ARYL HALIDES; BOND ACTIVATION; Sonogashira reaction; fluorine
• ISSN: 0947-6539; 1521-3765; 1521-3765
• DOI: 10.1002/chem.202002888

We report herein a mild procedure for the copper‐catalyzed oxidative cross‐coupling of electron‐deficient polyfluorophenylboronate esters with terminal alkynes. This method displays good functional group tolerance and broad substrate scope, generating cross‐coupled alkynyl(fluoro)arene products in moderate to excellent yields. Thus, it represents a simple alternative to the conventional Sonogashira reaction. BFF: A mild procedure is reported for the synthesis of alkynyl(fluoro)arenes via copper‐catalyzed oxidative cross‐coupling of polyfluorophenylboronate esters with terminal alkynes.