An Efficient Protocol for Selective Silylation of Hydroxy Group Using N,O-Bis(tert-butyldimethylsilyl)acetamide and N,N-Dimethyl-4-aminopyridine N-Oxide

Hiroki Mandai, Yuichiro Matsuura, Fatin Mahfuzah Binti Johari, Koichi Mitsudo, Seiji Suga

Research output: Contribution to journalArticlepeer-review

Abstract

An efficient method for the silylation of alcohols was developed using N,O-bis(tert-butyldimethylsilyl)acetamide (BTBSA) and 3mol% of N,N-dimethyl-4-aminopyridine Noxide (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.

Original languageEnglish
Pages (from-to)953-956
Number of pages4
JournalChemistry Letters
Volume51
Issue number9
DOIs
Publication statusPublished - Sep 2022

Keywords

  • Chemoselective silylation
  • DMAPO
  • Organocatalyst

ASJC Scopus subject areas

  • Chemistry(all)

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