121st General Meeting of the KCS

Type Poster Presentation
Area Organic Chemistry
Room No. Event Hall
Time 4월 19일 (목요일) 11:00~12:30
Code ORGN.P-491
Subject An Efficient Cyanation of Aryl and Vinyl halides via Modified Rosenmund-von Braun Reaction
Authors Heung Bae Jeon*, Meehee Bang1, Haelim Cho2, HANA LEE1, YEONJI KIM2
Department of Chemistry, Kwangwoon University, Korea
1Kwangwoon University, Korea
2Chemistry, Kwangwoon University, Korea
Abstract Aryl and α,β-Unsaturated nitriles are present as a key motif of natural products, pharmaceuticals, agrochemicals, dyes, and herbicides. Moreover, the nitriles are employed as the versatile intermediates for the preparation of amines, amides, aldehydes, and carboxylic acids. The most popular synthetic method is the classical Rosenmund-von Braun reaction. However, it has the disadvantage of requiring high temperatures. The transition metal-mediated cyanation reactions have been more and more attractive in these years, among which palladium and copper are most commonly involved. Nevertheless, most such conventional homogeneous systems involve the use of expensive additional ligands. In order to solve this problem, we have studied an efficient and easy operational copper-mediated cyanation reaction of a wide variety of aryl and vinyl halides via the modified Rosenmund-Von Braun reaction. Herein we present the successful cyanation of lots of aryl halides and vinyl halides with copper cyanide and tetramethylethylenediamide (TMEDA) in poly(ethylene glycol) dimethyl ether (PEG250-(OMe)2) at 90-120 ℃. Our new method gave the aryl and α,β-Unsaturated nitriles in much better yields than that of original Rosenmund-von Braun reaction under mild reaction conditions and used readily available cheap reagents.
E-mail mehee0306@naver.com