Sept 2015 - Article in Adv. Synth. Catal. Published

James' paper comparing the efficiencies of various organocatalysts for acylation, sulfonylation and silylation of alcohols is published.

James I. Murray and Alan C. Spivey* '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', Adv. Synth. Catal., 2015, 357, 3825-3830. DOI: 10.1002/adsc.201500773

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-methyl-imidazole-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 tert-alcohols in high yield with low catalyst loading under mild reaction conditions.