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Arylphosphonate-Directed Ortho C–H Borylation: Rapid Entry into Highly-Substituted Phosphoarenes

Feiyang Xu, Olivia M. Duke, D. Rojas, Hanka M. Eichelberger, Raphael S. Kim, Timothy B. Clark, Donald A. Watson

2020Journal of the American Chemical Society41 citationsDOIOpen Access PDF

Abstract

Phosphonate-directed ortho C–H borylation of aromatic phosphonates is reported. Using simple starting materials and commercially accessible catalysts, this method provides steady access to o-phosphonate arylboronic esters bearing pendant functionality and flexible substitution patterns. These products serve as flexible precursors for a variety of highly substituted phosphoarenes, and in situ downstream functionalization of the products is described.

Topics & Concepts

BorylationChemistryPhosphonateCombinatorial chemistrySurface modificationCatalysisOrganic chemistryArylAlkylPhysical chemistryOrganoboron and organosilicon chemistryOrganophosphorus compounds synthesisCatalytic C–H Functionalization Methods
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