Combining Gold(I)/Gold(III) Catalysis and C-H Functionalization: A Formal Intramolecular [3+2] Annulation towards Tricyclic Indolines and Mechanistic Studies

被引：117

作者：

Zhang, Guozhu ^{[1
]}

Luo, Yingdong ^{[1
]}

Wang, Yanzhao ^{[1
]}

Zhang, Liming ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 19期

关键词：

gold; homogeneous catalysis; nitrogen heterocycles; oxidation; reaction mechanisms; CROSS-COUPLING REACTIONS; NONACTIVATED ARENES; GOLD CATALYSIS; BOND FORMATION; ALKENES; ACTIVATION; CYCLIZATION; REACTIVITY; COMPLEXES; EFFICIENT;

D O I：

10.1002/anie.201100293

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Gold rush: A combination of oxidative gold(I)/gold(III) catalysis and C-H functionalization led to the first oxidative coupling between in situ generated alkyl gold reagents and C sp 2-H bonds, affording tricyclic indolines through a formal [3+2] annulation between a vinyl group and an aniline moiety [see scheme; Tf=trifluoromethanesulfonyl, Selectfluor=1-chloromethyl-4-fluoro-1,4- diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)]. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4450 / 4454

页数：5

共 48 条

[1]

[Anonymous], ANGEW CHEM

[2] Arylsilanes: Application to Gold-Catalyzed Oxyarylation of Alkenes [J].

Ball, Liam T. ;

Green, Michael ;

Lloyd-Jones, Guy C. ;

Russell, Christopher A. .

ORGANIC LETTERS, 2010, 12 (21) :4724-4727

[3]

Brand J. P., 2009, ANGEW CHEM, V121, P9510

[4] Direct Alkynylation of Indole and Pyrrole Heterocycles [J].

Brand, Jonathan P. ;

Charpentier, Julie ;

Waser, Jerome .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9346-9349

[5]

Brenzovich W. E., 2010, ANGEW CHEM, V122, P5651

[6] Gold-Catalyzed Oxidative Coupling Reactions with Aryltrimethylsilanes [J].

Brenzovich, William E., Jr. ;

Brazeau, Jean-Francois ;

Toste, F. Dean .

ORGANIC LETTERS, 2010, 12 (21) :4728-4731

[7] Gold-Catalyzed Intramolecular Aminoarylation of Alkenes: C-C Bond Formation through Bimolecular Reductive Elimination [J].

Brenzovich, William E., Jr. ;

Benitez, Diego ;

Lackner, Aaron D. ;

Shunatona, Hunter P. ;

Tkatchouk, Ekaterina ;

Goddard, William A., III ;

Toste, F. Dean .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (32) :5519-5522

[8] Supported gold catalyzes the homocoupling of phenylboronic acid with high conversion and selectivity [J].

Carrettin, S ;

Guzman, J ;

Corma, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (15) :2242-2245

[9]

Carrettin S., 2005, ANGEW CHEM, V117, P2282

[10] Homogeneous gold-catalyzed efficient oxidative dimerization of propargylic acetates [J].

Cui, Li ;

Zhang, Guozhu ;

Zhang, Liming .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (14) :3884-3887

← 1 2 3 4 5 →