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Catalytic Borylation using an Air‐Stable Zinc Boryl Reagent: Systematic Access to Elusive Acylboranes
Author(s) -
Campos Jesús,
Aldridge Simon
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201507627
Subject(s) - borylation , negishi coupling , reagent , chemistry , palladium , catalysis , zinc , steric effects , combinatorial chemistry , organic chemistry , aryl , alkyl
The use of borylzinc reagents in palladium‐catalyzed borylation chemistry is described (i.e. a boron analogue of the Negishi coupling), including a one‐pot bench‐top protocol using an air‐ and moisture‐stable bis(boryl)zinc reagent. The steric/electronic properties of the boryl fragment employed enable a systematic method for accessing acylboranes, a rare class of organoboron species with great potential in chemical synthesis. The reactions proceed under mild conditions, use inexpensive commercial sources of palladium, and demonstrate a remarkable functional‐group tolerance.