para-Methoxybenzyl methyl ether acts as an alkylating agent for thiols in the presence of trimethylsilyl trifluoromethanesulfonate and trialkylamine base in good yields (58-96%). Aryl ketones are alkylated under similar conditions, probably through an enol silane intermediate, also in high yields (67-95%). The active alkylating species is likely a p-methoxybenzyl cation.
Copyright © 2014, Elsevier. The definitive version is available at: http://www.journals.elsevier.com/tetrahedron-letters.
Downey, C. Wade, Sarah E. Covington, Derek C. Obenschain, Evan Halliday, James T. Rague, and Danielle N. Confair. "Silyl Trifluoromethanesulfonate-activated Para-methoxybenzyl Methyl Ether as an Alkylating Agent for Thiols and Aryl Ketones." Tetrahedron Letters 55, no. 37 (September 10, 2014): 5213-215. doi:10.1016/j.tetlet.2014.07.068.
Downey, C. Wade; Covington, Sarah E.; Obenschain, Derek C.; Halliday, Evan; Rague, James T.; and Confair, Danielle N., "Silyl trifluoromethanesulfonate-activated para-methoxybenzyl methyl ether as an alkylating agent for thiols and aryl ketones" (2014). Chemistry Faculty Publications. 14.