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

Chemical & Pharmaceutical Bulletin
Yukiko KaruoMunetaka Kunishima

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.

References

May 6, 2006·The Journal of Organic Chemistry·Kevin W C Poon, Gregory B Dudley
Oct 26, 2011·Organic & Biomolecular Chemistry·Teng-wei WangGregory B Dudley
Sep 22, 2012·Organic Letters·Kohei YamadaMunetaka Kunishima
Aug 12, 2014·Chemistry : a European Journal·Kohei YamadaMunetaka Kunishima
Oct 13, 2015·The Journal of Organic Chemistry·Hikaru FujitaMunetaka Kunishima
Aug 17, 2016·Chemistry : a European Journal·Kohei YamadaMunetaka Kunishima
Jan 5, 2017·Chemical & Pharmaceutical Bulletin·Kohei YamadaMunetaka Kunishima

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Citations

Feb 1, 2020·Chemical Communications : Chem Comm·Mylène RichardBertrand Kuhnast

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