Pyrimidin‐6‐yl Trifluoroborate Salts as Versatile Templates for Heterocycle Synthesis. Issue 17 (17th March 2021)

• Record Type: Journal Article
• Authors: Cousins, David L.; Fricero, Prisca; Kopf, Kenji P. M.; McColl, Elliot J.; Czechtizky, Werngard; Lim, Yee Hwee; Harrity, Joseph P. A.
• Is Part Of: Angewandte Chemie international edition. Volume 60:Issue 17(2021)
• Page Start: 9412
• Page End: 9415
• Publication Date: 2021-03-17
• Subjects: chemoselective -- cross-coupling -- pyrimidine -- trifluoroborate; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202101297
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: We report a novel and general method to access a highly under‐studied privileged scaffold—pyrimidines bearing a trifluoroborate at C4, and highlight the broad utility of these intermediates in a rich array of downstream functionalization reactions. This chemistry is underpinned by the unique features of the trifluoroborate group; its robustness provides an opportunity to carry out chemoselective reactions at other positions on the pyrimidine while providing a pathway for elaboration at the C−B bond when suitably activated. Abstract : Stable and enabling: Pyrimidine trifluoroborates are an under‐developed scaffold that have been rarely reported in the literature. These compounds participate in a rich array of downstream functionalization reactions that are underpinned by the unique features of the trifluoroborate group; its robustness provides an opportunity to carry out chemoselective reactions at other positions on the pyrimidine while providing a pathway for elaboration at the C−B bond when activated.