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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.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Development of Triazine-Based Benzylating Reagents Possessing &lt;i&gt;t&lt;/i&gt;-Butyl Group on the Triazine Core: Thermally Controllable Reagents for the Initiation of Reaction