Leaving Group Effects on the Selectivity of the Silylation
of Alcohols: The Reactivity–Selectivity Principle Revisited
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Abstract
TBS
protection of primary alcohol naphthalen-1-ylmethanol (<b>4a</b>) and secondary alcohol 1-(naphthalen-1-yl)ethanol (<b>4b</b>) has been studied under various reaction conditions. The
primary/secondary selectivity is largest in the comparatively slow
Lewis base catalyzed silylation in apolar solvents and systematically
lower in DMF. Lowest selectivities (and fastest reaction rates) are
found for TBS triflate <b>1b</b>, where only minor effects of
solvent polarity or Lewis base catalysis can be observed