摘要
报道了铜催化的化学选择性N-烯基丙烯酰胺氰异丙基化/环化级联反应,利用该反应可以实现1,3-二氢吡咯-2-酮的合成.丙烯酰胺的自由基环合反应中,用于捕获分子内自由基的基团主要局限于芳基、炔基和氰基,而本工作使用烯胺双键作为内置自由基捕获基团,以丙烯酰胺双键作为自由基受体.该反应的化学选择性可能是由自由基反应的极性匹配原则决定.
A copper-catalyzed cyanoisopropylation/cyclization cascade of N-alkenylacrylamides is presented, providing a straightforward and chemoselective access to 1,3-dihydropyrrol-2-ones. In acrylamide-based radical cyclization, radical-trapping groups are mainly restricted to aryl, alkynyl or cyano group. But in this reaction, the enaminic double bond was used as an inbuilt radical trap, while the olefinic bond of the acrylamidyl moiety acted as the radical acceptor. Such chemoselectivity might be attributed to polarity matching.
作者
戴恩睿
罗清
陈春琳
盈凤元
董英
刘颖杰
王宝玲
马银海
梁德强
Dai Enrui;Luo Qing;Chen Chunlina;Ying Fengyuan;Dong Ying;Liu Yingjie;Wang Baoling;Ma Yinhai;Liang Deqiang(Department of Chemistry,Kunming University,Kunming 650214;College of Chemistry,Chemical Engineering and Materials Science,Shandong Normal University,Jinan 250014;Engineering Research Center for Medicine,Harbin University of Commerce College of Pharmacy,Harbin 150076;Yunnan Engineering Technology Research Center for Plastic Films,Kunming 650214)
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2019年第12期3524-3531,共8页
Chinese Journal of Organic Chemistry
基金
Project supported by the National Natural Science Foundation of China(No.21702083)
the Yunnan Ten Thousand Talent Program for Young Top-Notch Talents
the Program for Innovative Research Team(in Science and Technology)in Universities of Yunnan Province
the Applied Basic Research Programs of Yunnan Science and Technology Department(Nos.2018FD028,2018FH001-002)
the Excellent Youth Project of Heilongjiang Natural Science Foundation(No.UNPYSCT-2016181)
the Scientific Research Funds of Yunnan Education Department(No.2017ZDX048)
the Research Foundation for Introduced Talents of Kunming University(No.YJL19001)~~
