TBHP/NH4I‑Mediated Direct N–H Phosphorylation of Imines and Imidates

TBHP/NH4I‑Mediated Direct N–H Phosphorylation of Imines and Imidates

A direct and practical metal-free N–H phosphorylation has been achieved via the TBHP/NH4I-mediated cross-dehydrogenative coupling (CDC) reactions between imines/imidates and P­(O)H compounds. This transformation provides an efficient synthetic route to the construction of P–N bonds with good functio...

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Veröffentlicht in:Journal of organic chemistry 2019-11, Vol.84 (22), p.14949-14956
Hauptverfasser: Wang, Xiaofeng, Ou, Yingcong, Peng, Zhenbo, Yu, Guodian, Huang, Yuanting, Li, Xianwei, Huo, Yanping, Chen, Qian
Format: Artikel
Sprache:eng
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Zusammenfassung:A direct and practical metal-free N–H phosphorylation has been achieved via the TBHP/NH4I-mediated cross-dehydrogenative coupling (CDC) reactions between imines/imidates and P­(O)H compounds. This transformation provides an efficient synthetic route to the construction of P–N bonds with good functional group compatibility, leading to the formation of N-phosphoryl­imines and N-phosphoryl­imidates in up to 95% yield (33 examples) under mild conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02301