Stable Oxypyridinium Triflate (OPT) Salts for the Synthesis of Halobenzyl Ethers

Abstract

A collection of new oxypyridinium triflate reagents (1a–d) for the synthesis of halobenzyl ethers from alcohols under “mix‐and‐heat” conditions is described. The reagents are stable organic salts that can be stored indefinitely and handled without special precautions, making them attractive for general use in organic synthesis. Halobenzylation of representative alcohols occurs in good to excellent yield.

This paper is dedicated to Professor Ken Goldsby (FSU) for his promotion and support of undergraduate research.

Keywords:

• oxypyridinium salt
• p‐bromobenzyl
• p‐iodobenzyl
• p‐chlorobenzyl
• o‐bromobenzyl
• arylmethylation

Acknowledgment

This research was supported by the FSU Department of Chemistry and Biochemistry. S. M. A. and S. E. H. received Brautlecht Fellowships for summer undergraduate research. J. P. M. and M. E. M. contributed to the project in partial fulfillment of requirements for CHM 1051L, the laboratory component of Honors General Chemistry II. M. K. R. was a visiting undergraduate research associate from Smith College, Northampton, MA. We thank Professor Kevin Shea (Smith College) for helpful guidance and discussion. We thank Tom Gedris for assistance with the NMR facilities, Umesh Goli for the mass spectrometric analyses, and the Krafft Lab for use of their FT‐IR instrument.

Notes

This paper is dedicated to Professor Ken Goldsby (FSU) for his promotion and support of undergraduate research.