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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 29, Number 3
JKCSEZ 29(3)
June 20, 1985 

 
Title
Palladium Catalyzed Synthesis of Aryl Conjugated Enamides

팔라듐 촉매를 이용한 Aryl Conjugated Enamides의 합성
Author
Young Taik Hong, Jong Tae Lee, Cheol Mo Ryu, Jin Il Kim

홍영택, 이종태, 유철모, 김진일
Keywords
Abstract
Acrylamide, N-alkyl substituted acrylamides and N,N-diethylacrylamide를 트리에틸아민과 palladium acetate-triorthotolyl phosphine 촉매 존재하에서 브롬화 방향족화합물들과 비닐화 반응을 실시하여 여러 기능기로 치환된 aryl conjugated enamides를 합성하였다. 이들 반응은 모두 선택적으로 진행되어 (E)-이성질체의 aryl conjugated enamides를 생성하였다. N-alkyl substituted acrylamides는 브롬화 방향족화합물들과의 반응에서 acrylamide와 N,N-diethylacrylamide보다 더 좋은 반응성을 나타내어 생성물들을 높은 수득율로 얻을 수 있었다. 또한 브롬화 방향족화합물이 전자받기 기능기로 치환된 경우에 좋은 반응성을 나타냈으며 전자 주기 기능기를 갖는 경우 acrylamide와 N,N-diethylacrylamide와의 반응에서는 반응이 전혀 진행되지 않거나 낮은 반응성을 나타냈다.

Acrylamide, N-alkyl substituted acrylamides and N,N-diethylacrylamide were reacted with aryl bromides in the presence of triethylamine and palladium acetate-triorthotolyl phosphine catalyst to form the various substituted aryl conjugated enamides. These reactions proceeded selectively and (E)-isomer of aryl conjugated enamides was obtained. N-alkyl substituted acrylamides were more reactive than acrylamide or N,N-diethylacrylamide and gave high yields of vinylated products. Aryl bromides with electron withdrawing group showed good reactivity but aryl bromides with electron donating group showed poor reactivity or no reactivity for acrylamide or N,N-diethylacrylamide.

Page
287 - 294
Full Text
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