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C−H Activation Based Copper‐Catalyzed One‐Shot Synthesis of N,O‐Bidentate Organic Difluoroboron Complexes

Guangying Tan, Malte L. Schrader, Constantin G. Daniliuc, Felix Strieth‐Kalthoff, Frank Glorius

2020Angewandte Chemie International Edition43 citationsDOI

Abstract

Abstract Organic BF 2 complexes exhibit characteristics such as large Stokes shift, high quantum yield, strong emission intensity, and robust chemical stability, thereby being extensively used in various applications. Herein, we disclose a novel copper‐catalyzed cascade C−H activation/acyloxylation and difluoroboronation of 2‐phenylpyridine derivatives, thus providing a straightforward and rapid gateway to a series of N,O‐bidentate organic BF 2 complexes with excellent photophysical properties. Mechanism studies demonstrate that AgBF 4 services as BF 2 source and oxidant for this elegant transformation. Most of these BF 2 complexes have broad and intense absorption and emission bands, and display bright and intensive blue fluorescence as well as large Stokes shifts.

Topics & Concepts

DenticityQuantum yieldCopperChemistryPhotochemistryAbsorption (acoustics)FluorescenceStokes shiftCatalysisMaterials scienceCrystallographyOrganic chemistryOpticsPhysicsCrystal structureComposite materialCatalytic C–H Functionalization MethodsLuminescence and Fluorescent MaterialsFluorine in Organic Chemistry
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