Heterocyclization Approach for Electrooxidative Coupling of Functional Primary Alkylamines with Aromatics
作者:Tatsuya Morofuji、Akihiro Shimizu、Jun-ichi Yoshida
DOI:10.1021/jacs.5b06526
日期:2015.8.12
A new approach for electrooxidative coupling of aromatic compounds and primary alkylamines bearing a functional group such as a hydroxyl group and an amino group was developed. The key to the success of the transformation is heterocydization of functional primary alkylamines. Treatment of primary alkylamines bearing a functional group with nitriles or their equivalents gives the corresponding heterocycles. The electrochemical oxidation of aromatic substrates in the presence of the heterocycles followed by chemical reaction under nonoxidative conditions gave the desired coupling products.
A CONVENIENT SYNTHESIS OF IMIDAZOLIUM SALTS AND TRISUBSTITUTED ETHYLENEDIAMINE DERIVATIVES
A series of 1,2-dimethyl-3-arylsulfonyl1-4,5-dihydroimidazolium iodides (7–11) was prepared by convenient sulfonylation and methylation from commercially available 2-methyl-2-imidazoline. Trisubstituted ethylenediamine derivatives 12–21 were synthesized from the reduction or hydrolysis of imidazolium salts 7–11 in high yield.