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

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 h...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 49; pp. 9130 - 9134
Main Authors Yu, Kai-Cheng, Li, Hai, Tu, Yuan-Hong, Zhao, Hui, Hu, Xiang-Guo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.12.2022
Amer Chemical Soc
Subjects
Amines - chemistry
Chemistry
Chemistry, Organic
Copper - chemistry
Indicators and Reagents
Molecular Structure
Physical Sciences
Science & Technology
DESIGN
LIGANDS
PHOTOREDOX
CHEMISTRY
INHIBITORS
SINGLE-ELECTRON TRANSMETALATION
AMIDES
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03860