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Cu/Pd-Catalyzed <i>cis-</i>Borylfluoroallylation of Alkynes for the Synthesis of Boryl-Substituted Monofluoroalkenes

Ayman M. Y. Suliman, Ebrahim‐Alkhalil M. A. Ahmed, Tian‐Jun Gong, Yao Fu

2021Organic Letters71 citationsDOI

Abstract

Monofluoroalkenes normally act as metabolically stable bioisosteres for amide groups (−NH–CO−) and have widespread applications in drug discovery. Additionally, they are widely used as building blocks in organic synthesis. In this study, the Cu/Pd-catalyzed cis-borylfluoroallylation of alkynes was achieved, providing a modular and general tactic for the preparation of monofluorinated alkene scaffolds with high regioselectivity and stereoselectivity. Moreover, an array of synthetic building blocks can be generated by downstream transformations.

Topics & Concepts

ChemistryAlkeneRegioselectivityCatalysisStereoselectivityAmideCombinatorial chemistryModular designStereochemistryOrganic chemistryProgramming languageComputer scienceFluorine in Organic ChemistryOrganoboron and organosilicon chemistryCatalytic C–H Functionalization Methods
Cu/Pd-Catalyzed <i>cis-</i>Borylfluoroallylation of Alkynes for the Synthesis of Boryl-Substituted Monofluoroalkenes | Litcius