4.6 Article

Practical Synthesis of Phosphinic Amides/Phosphoramidates through Catalytic Oxidative Coupling of Amines and P(O)-H Compounds

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 4, Pages 881-887

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201904237

Keywords

late-stage functionalization; cross-coupling; phosphinic amides; phosphoramidates; phosphorus

Funding

  1. Beijing Natural Science Foundation [2184115]
  2. National Natural Science Foundation of China [21702013]
  3. Fundamental Research Funds from the Central Universities in BUCT [XK1802-6, buctrc201721]

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Herein, we report a highly efficient ZnI2-triggered oxidative cross-coupling reaction of P(O)-H compounds and amines. This operationally simple protocol provides unprecedented generic access to phosphinic amides/phosphoramidate derivatives in good yields and short reaction time. Besides, the reaction proceeds under mild conditions, which avoids the use of hazardous reagents, and is applicable to scale-up syntheses as well as late-stage functionalization of drug molecules. The stereospecific coupling is also achieved from readily available optically enriched P(O)-H compounds.

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