Intramolecular Palladium-Catalyzed Oxidative Amination of Furans: Synthesis of Functionalized Indoles

被引：17

作者：

Makarov, Anton S. ^{[1
]}

Uchuskin, Maxim G. ^{[1
]}

Gevorgyan, Vladimir ^{[2
]}

机构：

[1] Perm State Univ, Dept Chem, Bukireva 15, Perm 614990, Russia

[2] Univ Illinois, Dept Chem, 845 West Taylor St, Chicago, IL 60607 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 22期

基金：

俄罗斯基础研究基金会;

关键词：

WACKER-TYPE CYCLIZATION; C-H ACTIVATION; NATURAL-PRODUCTS; SIMPLE ROUTE; RING; AROMATICITY; DEAROMATIZATION; TRANSFORMATION; ALCOHOLS; OLEFINS;

D O I：

10.1021/acs.joc.8b02470

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unconventional modification of palladium-catalyzed oxidative amination where a furan ring serves as a masked olefin is described. The designed chemical process provides 2-(2-acylvinyl)indole derivatives with up to a 93% yield and excellent E-selectivity. A highly reactive alpha,beta-unsaturated carbonyl moiety of the obtained compounds allows for accessing various heteroaromatic scaffolds through simple synthetic procedures.

引用

页码：14010 / 14021

页数：12

共 64 条

[1] The Butin reaction [J].

Abaev, Vladimir T. ;

Trushkov, Igor V. ;

Uchuskin, Maxim G. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (12) :973-995

[2] A Simple Route to Polysubstituted Indoles Exploiting Azide Induced Furan Ring Opening [J].

Abaev, Vladimir T. ;

Plieva, Anastasiya T. ;

Chalikidi, Petrakis N. ;

Uchuskin, Maxim G. ;

Trushkov, Igor V. ;

Butin, Alexander V. .

ORGANIC LETTERS, 2014, 16 (16) :4150-4153

[3] Pd(II)-catalyzed enantioselective intramolecular oxidative amination utilizing (+)-camphorsulfonic acid [J].

Aebly, Andrew H. ;

Rainey, Trevor J. .

TETRAHEDRON LETTERS, 2017, 58 (40) :3795-3799

[4] The complexity of catalysis: origins of enantio- and diastereocontrol in sulfur ylide mediated epoxidation reactions [J].

Aggarwal, VK ;

Richardson, J .

CHEMICAL COMMUNICATIONS, 2003, (21) :2644-2651

[5] PALLADIUM-PROMOTED ADDITION OF AMINES TO ISOLATED DOUBLE-BONDS [J].

AKERMARK, B ;

BACKVALL, JE ;

HEGEDUS, LS ;

ZETTERBE.K ;

SIIRALAH.K ;

SJOBERG, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 72 (01) :127-138

[6] Control of kinetics and thermodynamics of [1,5]-shifts by aromaticity: A view through the prism of Marcus theory [J].

Alabugin, IV ;

Manoharan, M ;

Breiner, B ;

Lewis, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) :9329-9342

[7] Aromaticity as a cornerstone of heterocyclic chemistry [J].

Balaban, AT ;

Oniciu, DC ;

Katritzky, AR .

CHEMICAL REVIEWS, 2004, 104 (05) :2777-2812

[8]

Barden T. C., 2010, TOPICS HETEROCYCLIC, P31

[9] Organocatalytic enantioselective nucleophilic vinylic substitution by α-substituted-α-cyanoacetates under phase-transfer conditions [J].

Bell, Mark ;

Poulsen, Thomas B. ;

Jorgensen, Karl Anker .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (08) :3053-3056

[10] Intra-Intermolecular Palladium-Catalyzed Domino Reactions of Glycine Allylamides for the Synthesis of Diversely Functionalized Piperazinones [J].

Broggini, Gianluigi ;

Beccalli, Egle M. ;

Borelli, Tea ;

Brusa, Filippo ;

Gazzola, Silvia ;

Mazza, Alberto .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (19) :4261-4268

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