Synthesis 2020; 52(07): 1140-1146
DOI: 10.1055/s-0039-1690795
paper
© Georg Thieme Verlag Stuttgart · New York

Solvent-Free and Liquid-Phase Iodination of Thiophene Derivatives with Potassium Dichloroiodate Monohydrate

a   Department of Chemistry, University of South Dakota, Vermillion, SD 57069, USA   Email: akash.mamon@gmail.com   Email: grigoriy.sereda@usd.edu
,
a   Department of Chemistry, University of South Dakota, Vermillion, SD 57069, USA   Email: akash.mamon@gmail.com   Email: grigoriy.sereda@usd.edu
,
Anwar Hussain
a   Department of Chemistry, University of South Dakota, Vermillion, SD 57069, USA   Email: akash.mamon@gmail.com   Email: grigoriy.sereda@usd.edu
,
Nikolai Zefirov †
b   Department of Chemistry, Moscow State University, Moscow 119899, Russian Federation
› Author Affiliations
Funding from the University of South Dakota Department of Chemistry is appreciated.
Further Information

Publication History

Received: 13 October 2019

Accepted after revision: 29 December 2019

Publication Date:
23 January 2020 (online)


Deceased

Abstract

Iodination of a series of benzene and thiophene derivatives by potassium dichloroiodate monohydrate was studied with and without a solvent. The liquid substrates tend to be more reactive in water while the solid substrates afford better yields in dichloromethane or under the solvent-free conditions. The 2-substituted thiophenes show good to excellent yields whereas the yield for 3-substituted and 3,4- or 2,4-disubstituted thiophenes and benzene derivatives are significantly lower. The mechanochemical reaction of 5-carbaldehyde-2,2′-bithiophene shows excellent yields, while 2,2′-bithiophene gives practical yields only in dichloromethane. In the case of thiophene and N-acetyl-p-toluidine, electrophilic iodination is accompanied by a small extent of chlorination.

Supporting Information