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Direct Synthesis of Dibenzophospholes from Biaryls by Double C–P Bond Formation via Phosphenium Dication Equivalents

Kazutoshi Nishimura, Koji Hirano, Masahiro Miura

2020Organic Letters44 citationsDOIOpen Access PDF

Abstract

We have developed a new strategy for the generation of phosphenium dication equivalents from readily available phosphinic acids and Tf2O. The in situ-generated dication equivalents can be readily coupled with simple (hetero)biaryls to form the corresponding dibenzophospholes directly. This protocol can also be applied to the concise synthesis of six- and seven-membered phosphacycles as well as the largely π-extended heteroacene derivatives, which are of great interest in the field of organic functional materials.

Topics & Concepts

DicationChemistryEquivalentDouble bondCombinatorial chemistryIn situStereochemistryMoleculeOrganic chemistryBiochemistrySynthesis and characterization of novel inorganic/organometallic compoundsCatalytic Cross-Coupling ReactionsOrganoboron and organosilicon chemistry
Direct Synthesis of Dibenzophospholes from Biaryls by Double C–P Bond Formation via Phosphenium Dication Equivalents | Litcius