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DOI: 10.1055/s-0040-1707135
Aerobic C–H Functionalization Using Pyrenedione as the Photocatalyst
Funding was provided by the National University of Singapore, the Ministry of Education (MOE) of Singapore (MOE2014-T2-1-134, MOE2017-T2-2-081) and the Natural Science Foundation of Jiangsu Province, P. R. of China (BK20141219).Publication History
Received: 27 March 2020
Accepted after revision: 05 May 2020
Publication Date:
02 June 2020 (online)
Abstract
We disclose a visible-light-promoted aerobic alkylation of activated C(sp3)–H bonds using pyrenedione (PYD) as the photocatalyst. Direct C–H bond alkylation of tetrahydrofuran with alkylidenemalononitriles is accomplished in over 90% yield in the presence of 5 mol% of PYD and 18 W blue LED light under ambient conditions. The substrate scope is extended to ethers, thioethers, and allylic C–H bonds in reactions with various electrophilic Michael acceptors. The catalytic turnover process is facilitated by oxygen. Our work represents the first example of using PYD as a photocatalyst to promote C(sp3)–H alkylation, revealing the unique character of PYD as a novel organophotocatalyst.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707135.
- Supporting Information
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