Pyrrole Synthesis via Allylic sp3 C-H Activation of Enamines Followed by Intermolecular Coupling with Unactivated Alkynes

被引：536

作者：

Rakshit, Souvik ^{[1
]}

Patureau, Frederic W. ^{[1
]}

Glorius, Frank ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, NRW Grad Sch Chem, D-48149 Munster, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 28期

关键词：

BOND FORMATION; EFFICIENT SYNTHESIS; POLYSUBSTITUTED PYRROLES; SUBSTITUTED PYRROLES; CATALYZED REACTION; CONSTRUCTION; CYCLIZATION; INDOLES; IMINES; COUPLING/CYCLIZATION;

D O I：

10.1021/ja104305s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A conceptually novel pyrrole synthesis is reported, efficiently merging enamines and (unactivated) alkynes under oxidative conditions. In an intermolecular Rh catalyzed process, the challenging allylic sp(3) C-H activation of the enamine substrates is followed by the cyclization with the alkyne (R-3 = CO2R). Alternatively, in some cases (R-3 = CN), the enamine can be utilized for a vinylic sp(2) C-H activation. A total of 17 examples with yields above 60% is presented, together with the results of an initial mechanistic investigation.

引用

页码：9585 / 9587

页数：3

共 43 条

[1] An Extremely Facile Synthesis of Furans, Pyrroles, and Thiophenes by the Dehydrative Cyclization of Propargyl Alcohols [J].

Aponick, Aaron ;

Li, Chuan-Ying ;

Malinge, Jeremy ;

Marques, Emerson Finco .

ORGANIC LETTERS, 2009, 11 (20) :4624-4627

[2] Pyrrole syntheses by multicomponent coupling reactions [J].

Balme, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6238-6241

[3] Recent Advances in the Synthesis of Indole and Quinoline Derivatives through Cascade Reactions [J].

Barluenga, Jose ;

Rodriguez, Felix ;

Fananas, Francisco J. .

CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (07) :1036-1048

[4] Copper-Catalyzed C-C Bond Formation through C-H Functionalization: Synthesis of Multisubstituted Indoles from N-Aryl Enaminones [J].

Bernini, Roberta ;

Fabrizi, Giancarlo ;

Sferrazza, Alessio ;

Cacchi, Sandro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (43) :8078-8081

[5] Synthesis of highly substituted pyrroles via a multimetal-catalyzed rearrangement-condensation-cyclization Domino approach [J].

Binder, JT ;

Kirsch, SF .

ORGANIC LETTERS, 2006, 8 (10) :2151-2153

[6] Synthesis of dihydropyridines and pyridines from Imines and alkynes via C-H activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3645-3651

[7] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (02) :624-655

[8] Organocatalysis by N-heterocyclic, carbenes [J].

Enders, Dieter ;

Niemeier, Oliver ;

Henseler, Alexander .

CHEMICAL REVIEWS, 2007, 107 (12) :5606-5655

[9] Intermolecular rhodium-catalyzed [3+2+2] carbocyclization of alkenylidenecyclopropanes with activated alkynes:: Regio- and diastereoselective construction of cis-fused bicycloheptadienes [J].

Evans, P. Andrew ;

Inglesby, Phillip A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (39) :12838-+

[10] Lamellarins and related pyrrole-derived alkaloids from marine organisms [J].

Fan, Hui ;

Peng, Jiangnan ;

Hamann, Mark T. ;

Hu, Jin-Feng .

CHEMICAL REVIEWS, 2008, 108 (01) :264-287

← 1 2 3 4 5 →