Home
Resources
Publications
Difunctionalization of Alkenes Using 1-Chloro-1,2-benziodoxol-3-(1H)-one

Difunctionalization of Alkenes Using 1-Chloro-1,2-benziodoxol-3-(1H)-one

Hiromichi Egami, Takahiro Yoneda, Minako Uku, Takafumi Ide, Yuji Kawato, Yoshitaka Hamashima

J Org Chem. 2016 May 20;81(10):4020-30.

PMID: 27100051

Abstract:

Difunctionalization of alkenes with 1-chloro-1,2-benziodoxol-3-(1H)-one (1) was investigated. Various additional nucleophiles were tested, and oxychlorination, dichlorination, azidochlorination, chlorothiocyanation, and iodoesterfication were demonstrated. The oxychlorination product was obtained efficiently when the reaction was operated in water. Dichlorination occurred in the presence of a Lewis basic promoter, such as 4-phenylpyridine N-oxide, as an additive. The reaction with in situ-generated azido anion afforded azidochlorinated compounds with a chlorine atom at the terminal position, while the reaction with trimethylsilyl isothiocyanate produced chlorothiocyanation adducts with a chlorine atom at the benzylic position. On the other hand, when 1 was treated with tetra-n-butylammonium iodide prior to the addition of alkenes, only iodoesterification occurred selectively. These mild reactions enable convenient site-selective difunctionalizations of substrates having two alkene moieties. NMR experiments suggested that the electrophilic reactive species in each reaction varied depending on the nature of the added nucleophile.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP36945081	n-Butylammonium iodide		36945-08-1	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: