Jump to main content
Jump to site search

Issue 19, 2019
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.


Social activity

Search articles by author

Spotlight

Advertisements