Phosphine-Directed CH Borylation Reactions: Facile and Selective Access to Ambiphilic Phosphine Boronate Esters

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 arylbo...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-07, Vol.53 (29), p.7589
Main Authors: Crawford, Kristina M, Ramseyer, Timothy R, Daley, Christopher J A, Clark, Timothy B
Format: Article
Language:English
Subjects:
Ligands
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Summary: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. [PUBLICATION ABSTRACT]
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201402868