Visible-Light-Induced Highly Site-Selective Direct C–H Phosphorylation of Pyrrolo[2,3‑d]pyrimidine Derivatives with H‑Phosphine Oxides

An efficient and highly regioselective C6-phosphorylation protocol for pyrrolo­[2,3-d]­pyrimidine (7-DAP) derivatives with various H-phosphine oxides induced by visible light at room temperature is described for the first time. This protocol has been successfully achieved by the combination of Na2-e...

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Veröffentlicht in:Journal of organic chemistry 2024-03, Vol.89 (5), p.2996-3009
Hauptverfasser: Zhang, Zhuo, Liu, Mingrui, Liu, Min, Pan, Chenhong, Mao, Zhengtong, Zhang, Xingxian
Format: Artikel
Sprache:eng
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Zusammenfassung:An efficient and highly regioselective C6-phosphorylation protocol for pyrrolo­[2,3-d]­pyrimidine (7-DAP) derivatives with various H-phosphine oxides induced by visible light at room temperature is described for the first time. This protocol has been successfully achieved by the combination of Na2-eosin Y as a photocatalyst and LPO as an oxidant under transition metal- and additive-free conditions. The broad substrate scope, good functional group tolerance, excellent regioselectivity, and air tolerant conditions make this process favorable for the functional modification of pyrrolo­[2,3-d]­pyrimidine scaffold and enrich the phosphorylated 7-DAP compounds for further biological evaluation.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02416