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Pyrimidin‐6‐yl Trifluoroborate Salts as Versatile Templates for Heterocycle Synthesis
Author(s) -
Cousins David L.,
Fricero Prisca,
Kopf Kenji P. M.,
McColl Elliot J.,
Czechtizky Werngard,
Lim Yee Hwee,
Harrity Joseph P. A.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202101297
Subject(s) - chemistry , surface modification , template , combinatorial chemistry , robustness (evolution) , pyrimidine , scaffold , catalysis , nanotechnology , organic chemistry , computer science , stereochemistry , materials science , biochemistry , database , gene
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.