A convenient catalytic oxidative 1,2-shift of arylalkenes for preparation of a-aryl ketones mediated by NaI

注册 English

A convenient catalytic oxidative 1,2-shift of arylalkenes for preparation of a-aryl ketones mediated by NaI

Min Zhu , Yang Zhao

Citation: Min Zhu, Yang Zhao. A convenient catalytic oxidative 1,2-shift of arylalkenes for preparation of a-aryl ketones mediated by NaI[J]. Chinese Chemical Letters, 2015, 26(2): 248-250. doi: 10.1016/j.cclet.2014.11.006 shu

shu

A convenient catalytic oxidative 1,2-shift of arylalkenes for preparation of a-aryl ketones mediated by NaI

Min Zhu ^{a,
,} ,
Yang Zhao ^b,

通讯作者: Min Zhu,

基金项目:
Financial support from the National Natural Science Foundation of China (No. 21072176) is greatly appreciated. (No. 21072176)

摘要: Using a catalytic amount of NaI and a stoichiometric oxidant Oxone^@, a convenient procedure has been developed for the catalytic oxidative 1,2-shift of arylalkenes in CH₃CN/H₂O at room temperature, which provides the corresponding a-aryl ketones in moderate to good yields. In this protocol, sodium iodide is first oxidized into hypoiodous acid, which reacts with arylalkene to afford iodohydrin. Then, the iodohydrin is transformed into the a-aryl ketone via an oxidative 1,2-shift rearrangement.

关键词:

English

A convenient catalytic oxidative 1,2-shift of arylalkenes for preparation of a-aryl ketones mediated by NaI

Min Zhu ^{a,
,} ,
Yang Zhao ^b,

1.
a College of Biological and Environmental Sciences, Zhejiang Shuren University, Hangzhou 310015, China;
2.
b Foreign Language School, Zhejiang Shuren University, Hangzhou 310015, China

Corresponding author: Min Zhu,

Received Date: 09 September 2014
Available Online: 08 November 2014
Fund Project:

Abstract: Using a catalytic amount of NaI and a stoichiometric oxidant Oxone^@, a convenient procedure has been developed for the catalytic oxidative 1,2-shift of arylalkenes in CH₃CN/H₂O at room temperature, which provides the corresponding a-aryl ketones in moderate to good yields. In this protocol, sodium iodide is first oxidized into hypoiodous acid, which reacts with arylalkene to afford iodohydrin. Then, the iodohydrin is transformed into the a-aryl ketone via an oxidative 1,2-shift rearrangement.

Key words:

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