Palladium-catalyzed regioselective azidation of allylic C-H bonds under atmospheric pressure of dioxygen

被引：47

作者：

Chen, Huoji ^{[1
]}

Yang, Wanfei ^{[1
]}

Wu, Wanqing ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 21期

基金：

中国国家自然科学基金;

关键词：

AEROBIC OXIDATIVE AMINATION; SERIAL LIGAND CATALYSIS; TERMINAL ALKENES; PRIMARY AZIDES; OLEFINS; FUNCTIONALIZATION; CARBOCYCLIZATION; HYDROAZIDATION; TRANSFORMATION; ALKYLATION;

D O I：

10.1039/c4ob00442f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed allylic azidation of alkenes with sodium azide under atmospheric pressure of dioxygen was developed. This methodology provides a new efficient and simple route for accessing allylic azides. Furthermore, the one-pot process consisting of Pd-catalyzed allylic azidation of alkenes and Cu-catalyzed 1,3-dipolar cycloaddition led directly to the 1,2,3-triazole from the alkene. The formed allylic azide can be also in situ reduced to the allylic amine or oxidized to the alkenyl nitrile.

引用

页码：3340 / 3343

页数：4

共 82 条

[1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[3] Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions [J].

Angell, Yu L. ;

Burgess, Kevin .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (10) :1674-1689

[4] C-H Bond Activation in Transition Metal Species from a Computational Perspective [J].

Balcells, David ;

Clot, Eric ;

Eisenstein, Odile .

CHEMICAL REVIEWS, 2010, 110 (02) :749-823

[5] Extremely Simple but Long Overlooked: Generation of α-Azido Alcohols by Hydroazidation of Aldehydes [J].

Banert, Klaus ;

Berndt, Christian ;

Firdous, Samia ;

Hagedorn, Manfred ;

Joo, Young-Hyuk ;

Rueffer, Tobias ;

Lang, Heinrich .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (52) :10206-10209

[6] Reductive Azidation of Carbonyl Compounds via Tosylhydrazone Intermediates Using Sodium Azide [J].

Barluenga, Jose ;

Tomas-Gamasa, Maria ;

Valdes, Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (24) :5950-5952

[7] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Sottocornola, Silvia .

CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365

[8] Pd-Catalyzed C-H Bond Functionalization on the Indole and Pyrrole Nucleus [J].

Beck, Elizabeth M. ;

Gaunt, Matthew J. .

C-H ACTIVATION, 2010, 292 :85-121

[9] Azide/alkyne-"click" reactions: Applications in material science and organic synthesis [J].

Binder, Wolfgang H. ;

Kluger, Christian .

CURRENT ORGANIC CHEMISTRY, 2006, 10 (14) :1791-1815

[10] Organic azides:: An exploding diversity of a unique class of compounds [J].

Bräse, S ;

Gil, C ;

Knepper, K ;

Zimmermann, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240

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