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：253

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

页码：11124 / 11128

页数：5

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