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Hiroki Mandai, Yuichiro Matsuura, Fatin Mahfuzah Binti Johari, Koichi Mitsudo, Seiji Suga, An Efficient Protocol for Selective Silylation of Hydroxy Group Using N,O-Bis(tert-butyldimethylsilyl)acetamide and N,N-Dimethyl-4-aminopyridine N-Oxide, Chemistry Letters, Volume 51, Issue 9, September 2022, Pages 953–956, https://doi.org/10.1246/cl.220281
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Abstract
An efficient method for the silylation of alcohols was developed using N,O-bis(tert-butyldimethylsilyl)acetamide (BTBSA) and 3 mol % of N,N-dimethyl-4-aminopyridine N-oxide (DMAPO). Monosilylation of 1,2-diols was successfully achieved with high chemoselectivity. In addition, several control experiments revealed that a phenolic hydroxy group was silylated much faster than a primary alcohol in both an inter- and intramolecular manner. The reactivity toward silylation under these systems might stem from the pKa of the hydroxy group.