Cs₂CO₃-promoted P-N coupling reaction of H-phosphoryl compounds with N-tosylhydrazones to afford N-phosphorylhydrazones via diazo intermediates

Abstract

The Cs₂CO₃-promoted P-N coupling reaction of H-phosphoryl compounds and N-tosylhydrazones is reported. Formally, this transformation represents an interesting example of exchanging the sulfur and phosphorus functionalities to convert N-tosylhydrazones to N-phosphorylhydrazones. The reaction may take place via the nucleophilic interception of the in-situ generated diazo intermediates by H-phosphoryl compounds at the terminal nitrogen atom.

GRAPHICAL ABSTRACT

KEYWORDS:

• H-phosphoryl compound
• N-tosylhydrazone
• diazo intermediate
• P-N bond formation

Acknowledgements

Financial support from the Postgraduate Research & Practice Innovation Program of Jiangsu Province (SJCX20_0361), NSFC and Nanjing Tech University is acknowledged.

Conflict of interest

There are no conflicts of interest to declare.

Additional information

Funding

Financial support from the Postgraduate Research & Practice Innovation Program of Jiangsu Province (SJCX20_0361), NSFC and Nanjing Tech University is acknowledged.