“…Recently, we have been involved in a number of studies evaluating the promoter free reactivity of trichloroacetimidate electrophiles with nitrogen [26,27], sulfur [28], and oxygen [29] nucleophiles. Carboxylic acids have been noted to be alkylated under promoterfree conditions via symbiotic activation by trichloroacetimidates that are precursors to stabilized carbocations, including the 2-phenylisopropyl [30,31], 4-methoxybenzyl [32], diphenylmethyl [33], and tert-butyl imidates [34]. Given that trichloroacetimidates are simple to prepare from inexpensive starting materials and that the esterifications often proceed under mild conditions without the need for an exogenous promoter or catalyst, the formation of TMSE esters using this chemistry was investigated.…”