Visible-Light-Driven Organophotocatalyzed Mono‑, Di‑, and Tri-C(sp3)–H Alkylation of Phosphoramides

Posted on 14.01.2021 - 04:15
A photocatalytic metal-free, visible-light-driven, highly atom-economic, direct multiple α-C­(sp3)–H alkylation of phosphoramides and thiophosphoramides is demonstrated under environmentally benign conditions. Economically viable and commercially available Eosin-Y is used as an HAT photocatalyst for mono-α-C­(sp3)–H alkylation of phosphoramide derivatives. Remarkably, di- and tri-C­(sp3)–H alkylation of phosphoramides and thiophosphoramides using an acridinium photocatalyst is reported with good yield and selectivity. Mechanistic studies reveal that monoalkylation of phosphoramides by Eosin-Y follows the HAT mechanism, whereas di- and tri-C­(sp3)–H alkylation by the acridinium photocatalyst follows the SET mechanism.

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Ghosh, Krishna Gopal; Das, Debabrata; Chandu, Palasetty; Sureshkumar, Devarajulu (2021): Visible-Light-Driven Organophotocatalyzed Mono‑, Di‑, and Tri-C(sp3)–H Alkylation of Phosphoramides. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.0c02695
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