Highly regioselective α-formylation and α-acylation of BODIPY dyes tandem cross-dehydrogenative coupling with deprotection

A metal-free C-H formylation and acylation of BODIPY dyes using a variety of dioxolane derivatives as aldehyde equivalents is reported, providing a postfunctionalization method for controllable synthesis of BODIPYs with carbonyl groups at 3,5-positions via a radical process. The photophysical proper...

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Veröffentlicht in:Organic & biomolecular chemistry 2019-05, Vol.17 (2), p.5121-5128
Hauptverfasser: Lv, Fan, Yu, Yang, Hao, Erhong, Yu, Changjiang, Wang, Hua, Boens, Noёl, Jiao, Lijuan
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Zusammenfassung:A metal-free C-H formylation and acylation of BODIPY dyes using a variety of dioxolane derivatives as aldehyde equivalents is reported, providing a postfunctionalization method for controllable synthesis of BODIPYs with carbonyl groups at 3,5-positions via a radical process. The photophysical properties of resultant dyes from this efficient one-pot, chemo- and site-selective transformation have been studied. An efficient protocol for the regioselective C-H α-formylation and α-acylation of BODIPY dyes using dioxolane derivatives as aldehyde equivalents is reported.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob00927b