Amines vs. N-Oxides as Organocatalysts for Acylation, Sulfonylation and Silylation of Alcohols: 1-Methylimidazole N-Oxide as an Efficient Catalyst for Silylation of Tertiary Alcohols

作者：Murray James I; Spivey Alan C^*

来源：Advanced Synthesis & Catalysis, 2015, 357(18): 3825-3830.

DOI：10.1002/adsc.201500773

• acylation
• Lewis base catalysis
• 1-methylimidazole N-oxide
• organocatalysis
• silylation
• sulfonylation

A comparison of the relative catalytic efficiencies of Lewis-basic amines vs. N-oxides for the acylation, sulfonylation and silylation of primary, secondary and tertiary alcohols is reported. Whilst the amines are generally superior to the N-oxides for acylation, the N-oxides are superior for sulfonylation and silylation. In particular, 1-methylimidazole N-oxide (NMI-O) is found to be a highly efficient catalyst for sulfonylation and silylation reactions. To the best of our knowledge, NMI-O is the first amine or N-oxide Lewis basic organocatalyst capable of promoting the efficient silylation of tertalcohols in high yield with low catalyst loading under mild reaction conditions.

• 出版日期2015-12-14