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

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

A photoredox-mediated route to enamination of boron dipyrromethene (BODIPY) dyes with aliphatic amines is reported by activating both the β-C­(sp3)–H bond of amines and the α-C­(sp2)–H bond of BODIPYs under visible light illumination. Dehydrogenation of amines by excited-state BODIPYs and/or photore...

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Veröffentlicht in:Journal of organic chemistry 2020-07, Vol.85 (13), p.8360-8370
Hauptverfasser: Wang, Dandan, Guo, Xing, Wu, Hao, Wu, Qinghua, Wang, Hua, Zhang, Xiankang, Hao, Erhong, Jiao, Lijuan
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container_end_page 8370
container_issue 13
container_start_page 8360
container_title Journal of organic chemistry
container_volume 85
creator Wang, Dandan
Guo, Xing
Wu, Hao
Wu, Qinghua
Wang, Hua
Zhang, Xiankang
Hao, Erhong
Jiao, Lijuan
description A photoredox-mediated route to enamination of boron dipyrromethene (BODIPY) dyes with aliphatic amines is reported by activating both the β-C­(sp3)–H bond of amines and the α-C­(sp2)–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.
doi_str_mv 10.1021/acs.joc.0c00620
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title Visible Light Excitation of BODIPYs Enables Dehydrogenative Enamination at Their α‑Positions with Aliphatic Amines
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