期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 145, 期 3, 页码 1535-1541出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c12845
关键词
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Stable acyl azolium salts can undergo intermolecular HAT reaction upon LED irradiation to afford ketones.
Photoinduced hydrogen atom transfer (HAT) has been developed as a powerful tool to generate synthetically valuable radical species. The direct photoexcitation of ketones has been known to promote HAT or to generate acyl radicals through Norrish-type pathways, but these modalities remain severely limited by radical side reactions. We report herein a catalyst-and transition metal-free method for the acylation of C-H bonds that leverages the unique properties of stable, isolable acyl azolium species. Specifically, acyl azolium salts are shown to undergo an intermolecular and regioselective HAT upon LED irradiation with a range of substrates bearing active C-H bonds followed by C-C bond formation to afford ketones. Experimental and computational studies support photoexcitation of the acyl azolium followed by facile intersystem crossing to access triplet diradical species that promote selective HAT and radical-radical cross-coupling.
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