Journal
SYNLETT
Volume -, Issue 20, Pages 3360-3364Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1218370
Keywords
p-iodotoluene; Oxone (R); alpha-tosyloxyketone; ketone; p-toluenesulfonic acid; catalyst
Categories
Funding
- Ministry of Education, Science, Sports and Culture of Japan [20550033]
Ask authors/readers for more resources
Various alkyl aryl ketones, dialkyl ketones, and cycloheptanone were efficiently converted into the corresponding alpha-tosyloxy ketones in good yields by using Oxone (R) and p-toluenesulfonic acid monohydrate in the presence of p-iodotoluene in acetonitrile. 4-Methoxyacetophenone and 2-acetylthiophene bearing an electron-rich aromatic group could be also converted into the corresponding alpha-tosyloxyketones smoothly in good yields with the present method. Here, p-iodotoluene works as catalyst and p-[(hydroxy)(tosyloxy)]iodotoluene is formed in situ as a reactive species for the alpha-tosyloxylation of ketones. However, one equivalent of p-iodotoluene was required to obtain alpha-tosyloxyketones in good yields and was recovered in 80-20% yields, depending on the reaction conditions.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available