Synthesis of Diversely Functionalized Oxindoles Enabled by Migratory Insertion of Isocyanide to a Transient σ-Alkylpalladium(II) Complex

被引：142
作者：
Kong, Wangqing [1 ]
Wang, Qian [1 ]
Zhu, Jieping [1 ]
机构：
[1] Ecole Polytech Fed Lausanne, Lab Synth & Nat Prod, Inst Chem Sci & Engn, EPFL SB ISIC LSPN, BCH 5304, CH-1015 Lausanne, Switzerland
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 33期
基金：
瑞士国家科学基金会;
关键词：
asymmetric synthesis; heterocycles; multicomponent reactions; palladium; synthetic methods; PALLADIUM-CATALYZED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ALPHA-ISOCYANOACETAMIDES; MULTICOMPONENT SYNTHESIS; ORTHO-ALKYNYLANILINES; H FUNCTIONALIZATION; CALABAR ALKALOIDS; HECK REACTION; ARYL HALIDES; CYCLIZATION;
D O I：
10.1002/anie.201603950
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Palladium-catalyzed intramolecular carbopalladation of N-aryl acrylamides followed by migratory insertion of an isocyanide-coordinated C(sp(3))-Pd intermediate afforded an alkylimidoyl-PdII complex, which can be intercepted by a nucleophile, including heteroarenes. In addition to amides, the alkylimidoyl-PdII complex was successfully converted into esters, ketones, and bis-heterocyclic compounds. An unprecedented palladium-catalyzed enantioselective domino process involving isocyanide was also documented.
引用
收藏
页码：9714 / 9718
页数：5
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