Copper-Catalyzed C-H Oxidative Radical Functionalization and Annulation of Aniline-Linked 1,7-Enynes: Evidence for a 1,5-Hydride Shift Mechanism

被引：84
作者：
Hu, Ming
Zou, Hua-Xu
Song, Ren-Jie
Xiang, Jian-Nan [1 ]
Li, Jin-Heng [1 ]
机构：
[1] Hunan Univ, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 24期
关键词：
CARBONYL ALKYL BROMIDES; PAUSON-KHAND REACTION; ACTIVATED ALKENES; ALLYLIC ALCOHOLS; UNACTIVATED ALKENES; CASCADE; CYCLOADDITION; CYCLIZATION; N-ENYNES; CYANOMETHYLATION;
D O I：
10.1021/acs.orglett.6b03352
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new copper-catalyzed tandem C-H oxidative radical functionalization and annulation of aniline-linked 1,7-enynes with alkyl nitriles or acetone is described. This reaction allows the selective construction of 1H-cyclopenta[c]quinolines and benzo[j]phenanthridin-6(5H)-ones which rely on the substitution effect at the 2-position of the acrylamide moiety. The mechanism involving a 1,5-hydride shift process is proposed according to the control deuterium-labeled experiment.
引用
收藏
页码：6460 / 6463
页数：4
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