Electron transfer-induced coupling of haloarenes to styrenes and 1,1-diphenylethenes triggered by diketopiperazines and Potassium tert-butoxide

Eswararao Doni; Shengze Zhou; John A Murphy

doi:10.3390/molecules20021755

Electron transfer-induced coupling of haloarenes to styrenes and 1,1-diphenylethenes triggered by diketopiperazines and Potassium tert-butoxide

Molecules. 2015 Jan 22;20(2):1755-74. doi: 10.3390/molecules20021755.

Authors

Eswararao Doni¹, Shengze Zhou², John A Murphy³

Affiliations

¹ WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, UK. eswararao.doni@strath.ac.uk.
² WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, UK. shengze_zhou@hotmail.com.
³ WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, UK. john.murphy@strath.ac.uk.

Abstract

The coupling of haloarenes to styrenes and 1,1-diarylethenes has been achieved with potassium tert-butoxide in the presence of N,N'-dialkyldiketopiperazines. In contrast to previously reported reactions where phenanthroline has been used to mediate the reactions, the use of diketopiperazines can lead to either 1,1,2-triarylethenes or 1,1,2-triarylethanes, depending on the conditions used.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzhydryl Compounds / chemistry*
Butanols / chemistry
Catalysis
Diketopiperazines / chemistry*
Hydrogen-Ion Concentration
Iodobenzenes / chemistry*
Oxidation-Reduction
Stilbenes / chemical synthesis*
Styrenes / chemistry*

Substances

1,1-diphenylethene
Benzhydryl Compounds
Butanols
Diketopiperazines
Iodobenzenes
Stilbenes
Styrenes
tert-butoxide, potassium