A convenient method for the synthesis of fluorinated α-cyanoacetates via phase-transfer catalysis

Abstract

A simple and convenient method for the synthesis of fluorinated α-cyanoacetate derivatives has been developed by using electrophilic fluorination of allyl and benzyl substituted α-cyanoacetates with N-fluorobenzensulfonimide (NFSI) as electrophilic fluorinating agent via phase transfer catalysis. The reaction is transition metal free and carried out in aqueous and mild reaction conditions in the presence of readily available tetra-N-butylammonium iodide (TBAI) as phase-transfer catalyst.

Graphical Abstract

Keywords:

• α-Cyanoacetates
• electrophilic fluorination
• organofluorine compounds
• phase-transfer catalysis
• quaternary ammonium salts

Acknowledgments

The authors thank Sophisticated Instrumentation Center, Dr. Harisingh Gour University, Sagar, and IISER Bhopal for recording NMR spectral data and HRMS of our compounds. KJ is thankful to UGC for the award of MANF research fellowship.

Additional information

Funding

The authors are grateful to the University Grants Commission (UGC), New Delhi for Start-up grant (No. F.30-56/2014 BSR) and Science and Engineering Research Board (SERB), Govt. of India for EMR grant (EMR/2017/000234) as financial support.