Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: Regioselective and switchable C-H alkenylation and annulation of pyrroles

被引：324

作者：

Beck, EM ^{[1
]}

Grimster, NP ^{[1
]}

Hatley, R ^{[1
]}

Gaunt, MJ ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 08期

关键词：

D O I：

10.1021/ja058141u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A palladium catalyzed C-H bond functionalization system that operates under ambient and aerobic conditions can be used to alkenylate pyrroles with control of regioselectivty. A steric and electronic control strategy can be used to influence positional control in the C-H bond functionalization process that results in either the C2 or C3 alkenylated products. Air, molecular oxygen, or tBuOOBz can be used as reoxidant in this mild process, and the reaction works on a range of substrates. Finally a catalytic aerobic annulation strategy is described that can be controlled to produce cyclization at either the C2 or C3 positions, thus forming diverse pyrrole products. Copyright © 2006 American Chemical Society.

引用

收藏

页码：2528 / 2529

页数：2

相关论文

共 29 条

[1] Direct coupling of pyrroles with carbonyl compounds: Short enantioselective synthesis of (S)-Ketorolac [J].

Baran, PS ;

Richter, JM ;

Lin, DW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) :609-612

[2] Concise synthesis of (±)-rhazinilam through direct coupling [J].

Bowie, AL ;

Hughes, CC ;

Trauner, D .

ORGANIC LETTERS, 2005, 7 (23) :5207-5209

[3] N-(TRIISOPROPYLSILYL)PYRROLE - A PROGENITOR PAR EXCELLENCE OF 3-SUBSTITUTED PYRROLES [J].

BRAY, BL ;

MATHIES, PH ;

NAEF, R ;

SOLAS, DR ;

TIDWELL, TT ;

ARTIS, DR ;

MUCHOWSKI, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6317-6328

[4] A sulfoxide-promoted, catalytic method for the regioselective synthesis of allylic acetates from monosubstituted olefins via C-H oxidation [J].

Chen, MS ;

White, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (05) :1346-1347

[5] Palladium-catalyzed multicomponent coupling of alkynes, imines, and acid chlorides: A direct and modular approach to pyrrole synthesis [J].

Dhawan, R ;

Arndtsen, BA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) :468-469

[6] An efficient synthesis of lactacystin β-lactone [J].

Donohoe, TJ ;

Sintim, H ;

Sisangia, L ;

Harling, JD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (17) :2293-2296

[7]

Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO

[8]

2-6

[9] Catalytic C-H bond functionalization with palladium(II):: Aerobic oxidative annulations of indoles [J].

Ferreira, EM ;

Stoltz, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) :9578-9579

[10] Concise and practical synthesis of latrunculin A by ring-closing enyne-yne metathesis [J].

Fürstner, A ;

Turet, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (22) :3462-3466