Metallaphotoredox-Enabled Construction of the P(O)-N Bond from Aromatic Amines and P(O)-H Compounds

Org Lett. 2022 Dec 16;24(49):9130-9134. doi: 10.1021/acs.orglett.2c03860. Epub 2022 Dec 6.

Abstract

We have developed a dual copper/photoredox-catalyzed approach for the construction of the P(O)-N bond from commercially available aromatic amines and P(O)-H compounds. This metallaphotoredox method avoids toxic or corrosive reagents and does not require prefunctionalized substrates. The reaction has a broad substrate scope and is suitable for the synthesis of phosphonamides and phosphinamides, thus complementing the previous nonphotochemical approaches. The reaction is amenable to the direct modification of drug molecules and can be conducted on a gram scale.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines* / chemistry
  • Copper* / chemistry
  • Indicators and Reagents
  • Molecular Structure

Substances

  • Amines
  • Copper
  • Indicators and Reagents