Hydrogen trifluoro(pyridin-2-yl)boranuide

CAS 3077251-76-1, Cat. No EN300-53117556
Reagent for 2-pyridylation

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The reagent hydrogen trifluoro(pyridin-2-yl)boranuide functions as a stable 2-pyridyl coupling synthon. In Pd-catalyzed cross-coupling reactions¹, it enables efficient 2-pyridylation of aryl halides, solving long-standing instability issues associated with 2-pyridyl boronic acids. The zwitterionic pyridinium–trifluoroborate structure is air- and water-stable, resistant to protodeboronation, and can be handled on the bench without special precautions. Under optimized conditions, the reagent couples selectively with aryl bromides and chlorides, tolerating a wide range of functional groups including esters, ketones, ethers, halogens, CF₃ groups, heterocycles, and complex pharmaceutical scaffolds. The protocol shows high chemoselectivity for C–C bond formation at the 2-position of pyridine, with minimal homocoupling or decomposition. Comparative robustness tests demonstrate that this reagent significantly outperforms conventional 2-pyridyl nucleophiles (boronic acids, MIDA boronates, organozincs, and Grignards), making it a practical and general method for late-stage pyridine installation in medicinal and materials chemistry.

Synonyms: trifluoro(pyridin-1-ium-2-yl)borate; (pyridin-1-ium-2-yl)trifluoroborate