Use of a Readily Removable Auxiliary Group for the Synthesis of Pyrrolidones by the Palladium-Catalyzed Intramolecular Amination of Unactivated γ C(sp3)-H Bonds

被引：252
|
作者：
He, Gang [1 ]
Zhang, Shu-Yu [1 ]
Nack, William A. [1 ]
Li, Qiong [1 ]
Chen, Gong [1 ]
机构：
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 42期
基金：
美国国家科学基金会;
关键词：
auxiliary groups; CH amination; palladium; pyrrolidones; -lactams; C-H BONDS; COOPERATIVE CATALYSIS; COUPLING REACTIONS; NATURAL-PRODUCTS; AROMATIC AMIDES; FUNCTIONALIZATION; CONSTRUCTION; ACTIVATION; ARYLATION; ALKYLATION;
D O I：
10.1002/anie.201305615
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Easy on, easy off: Directing groups found to promote the palladium-catalyzed amination of γ C(sp3)-H and C(sp 2)-H bonds of secondary amides included 5-methoxy-8-aminoquinoline, which can be removed under mild conditions (see scheme; CAN=ceric ammonium nitrate). In conjunction with a β-C-H methylation or γ-C-H arylation step, the γ-C(sp3)-H amination provided access to complex pyrrolidones from readily available precursors. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：11124 / 11128
页数：5
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