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Phosphine‐Directed CH Borylation Reactions: Facile and Selective Access to Ambiphilic Phosphine Boronate Esters
Author(s) -
Crawford Kristina M.,
Ramseyer Timothy R.,
Daley Christopher J. A.,
Clark Timothy B.
Publication year - 2014
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.201402868
Subject(s) - borylation , phosphine , chemistry , borane , aryl , reactivity (psychology) , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis , medicine , alkyl , alternative medicine , pathology
Ambiphilic ligands have received considerable attention over the last two decades due to their unique reactivity as organocatalysts and ligands. The iridium‐catalyzed CH borylation of phosphines is described in which the phosphine is used as a directing group to provide selective formation of arylboronate esters with unique scaffolds of ambiphilic compounds. A variety of aryl and benzylic phosphines were subjected to the reaction conditions, selectively providing stable, isolable boronate esters upon protection of the phosphine as the borane complex. After purification, the phosphine‐substituted boronate esters could be deprotected and isolated in pure form.