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Issue 19, 2019
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Diacetyl as a “traceless” visible light photosensitizer in metal-free cross-dehydrogenative coupling reactions

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Abstract

Minisci alkylation is of prime importance for its applicability in functionalizing diverse heteroarenes, which are core structures in many bioactive compounds. In alkyl radical generation processes, precious metal catalysts, high temperatures and excessive oxidants are generally involved, which lead to sustainability and safety concerns. Herein we report a new strategy using diacetyl (2,3-butanedione) as an abundant, visible light-sensitive and “traceless” hydrogen atom abstractor to achieve metal-free cross-dehydrogenative Minisci alkylation under mild conditions. Mechanistic studies supported hydrogen atom transfer (HAT) between an activated C(sp3)–H substrate and diacetyl. Moreover, with the assistance of di-tert-butyl peroxide (DTBP), the scope of the reaction could be extended to strong aliphatic C–H bonds via diacetyl-mediated energy transfer. The robustness of this strategy was demonstrated by functionalizing complex molecules such as quinine, fasudil, nicotine, menthol and alanine derivatives.

Graphical abstract: Diacetyl as a “traceless” visible light photosensitizer in metal-free cross-dehydrogenative coupling reactions

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Supplementary files

Article information


Submitted
17 Dec 2018
Accepted
07 Apr 2019
First published
08 Apr 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 5018-5024
Article type
Edge Article

Diacetyl as a “traceless” visible light photosensitizer in metal-free cross-dehydrogenative coupling reactions

C. Huang, J. Li, W. Liu and C. Li, Chem. Sci., 2019, 10, 5018
DOI: 10.1039/C8SC05631E

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