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Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through CH Activation and Orthogonal Reactivity
Author(s) -
Demory Emilien,
Devaraj Karthik,
Orthaber Andreas,
Gates Paul J.,
Pilarski Lukasz T.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201503152
Subject(s) - aryne , reagent , aryl , reactivity (psychology) , chemistry , combinatorial chemistry , silylation , catalysis , fluoride , nanotechnology , organic chemistry , materials science , inorganic chemistry , medicine , alkyl , alternative medicine , pathology
(Pinacolato)boryl ortho ‐silyl(hetero)aryl triflates are presented as a new class of building blocks for arylation. They demonstrate unique versatility by delivering boronate or (hetero)aryne reactivity chemoselectively in a broad range of transformations. This approach enables the unprecedented postfunctionalization of fluoride‐activated (hetero)aryne precursors, for example, as substrates in transition‐metal catalysis, and offers valuable new possibilities for aryl boronate postfunctionalization without the use of specialized protecting groups.