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CuF2/MeOH-Catalyzed N3-Selective Chan-Lam Coupling of Hydantoins: Method and Mechanistic Insight

Tanumay Roy, Krishanu Mondal, Arunava Sengupta and Parthasarathi Das*

*Department of Chemistry and Chemical Biology, Indian Institute of Technology (Indian School of Mines), Dhanbad 826004, India, Email: parthaiitism.ac.in

T. Roy, K. Mondal, A. Sengupta, P. Das, J. Org. Chem., 2023, 88, 6058-6070.

DOI: 10.1021/acs.joc.3c00408


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Abstract

The combination of CuF2/MeOH mediates an efficient, practical, and general N-arylation of hydantoins with substituted aryl/heteroaryl boronic acids under base and ligand-free conditions at room temperature and open air. Various N-arylated hydantoins have been prepared in excellent yields with exclusive regioselectivity. A selective N3-arylation of 5-fluorouracil nucleosides is also reported.


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proposed mechanism



Key Words

Chan-Lam Coupling, Hydantoins


ID: J42-Y2023