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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
Author(s) -
Murray James I.,
Spivey Alan C.
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500773
Subject(s) - silylation , chemistry , acylation , catalysis , organic chemistry , lewis acids and bases , yield (engineering) , tertiary amine , oxide , amine gas treating , tertiary alcohols , medicinal chemistry , materials science , metallurgy
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 tert ‐alcohols in high yield with low catalyst loading under mild reaction conditions.