Visible Light Excitation of BODIPYs Enables Dehydrogenative Enamination at Their α-Positions with Aliphatic Amines.

J Org Chem

Laboratory of Functional Molecular Solids, Ministry of Education; School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, China.

Published: July 2020

A photoredox-mediated route to enamination of boron dipyrromethene (BODIPY) dyes with aliphatic amines is reported by activating both the β-C(sp)-H bond of amines and the α-C(sp)-H bond of BODIPYs under visible light illumination. Dehydrogenation of amines by excited-state BODIPYs and/or photoredox catalyst gave enamine intermediates, which were further trapped by BODIPYs to give a series of α-enamineBODIPYs. These resultant α-enamineBODIPYs showed red-shifted absorption and emission maxima with ratiometric pH-dependent fluorescence.

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http://dx.doi.org/10.1021/acs.joc.0c00620DOI Listing

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