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Development of Triazine-Based Benzylating Reagents Possessing t-Butyl Group on the Triazine Core: Thermally Controllable Reagents for the Initiation of Reaction.

Authors
  • Karuo, Yukiko1
  • Yamada, Kohei1
  • Kunishima, Munetaka1
  • 1 Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University.
Type
Published Article
Journal
Chemical and Pharmaceutical Bulletin
Publisher
Pharmaceutical Society of Japan
Publication Date
Jan 01, 2018
Volume
66
Issue
3
Pages
303–308
Identifiers
DOI: 10.1248/cpb.c17-00897
PMID: 29491263
Source
Medline
Keywords
License
Unknown

Abstract

Benzylating reagents, 4-(4,6-di-t-butyl-1,3,5-triazin-2-yl)-4-benzylmorpholinium triflate, and related derivatives have been developed. The reagents release benzyl triflate as a benzyl cation equivalent upon heating the solution to 40°C under neutral conditions. The O-benzylation of alcohols using a stoichiometric amount of these reagents afforded corresponding benzyl ethers in good to high yields. This was due to the presence of a bulky t-butyl group on the triazine ring of these reagents that prevents the consumption of benzyl triflate via a side reaction with a morpholinotriazine derivative.

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