Development of a Palladium-Catalyzed Process for the Synthesis of Z-Alkenes by Sequential Sonogashira-Hydrogenation Reaction

被引：5

作者：

Hancker, Soeren ^{[1
]}

Neumann, Helfried ^{[1
]}

Beller, Matthias ^{[1
]}

机构：

[1] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 38期

关键词：

Palladium; Z-Alkenes; Homogeneous catalysis; Heterogeneous catalysis; Sonogashira coupling; Hydrogenation; SELECTIVE SEMIHYDROGENATION; POROUS CARBON; EFFICIENT; ALKYNES; PERFORMANCE; PYROLYSIS; COMPLEXES;

D O I：

10.1002/ejoc.201800651

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and selective sequential one-pot protocol for the synthesis of Z-alkenes via Sonogashira-semihydrogenation is reported. The efficiency of the methodology is increased by utilizing PdCl2/BuPAd(2) as homogeneous catalyst for the Sonogashira coupling and subsequently transforming the transition metal complex into a heterogeneous Pd hydrogenation catalyst. This methodology represents one of the rare examples directly combining homogeneous and heterogeneous catalysis.

引用

页码：5253 / 5259

页数：7

共 47 条

[1] Synthesis, crystal structures, and application of two new pincer type palladium(II)-Schiff base complexes in C-C cross-coupling reactions [J].

Agrahari, Bhumika ;

Layek, Samaresh ;

Anuradha ;

Ganguly, Rakesh ;

Pathak, Devendra D. .

INORGANICA CHIMICA ACTA, 2018, 471 :345-354

[2]

Baumeister P, 1997, CHIMIA, V51, P144

[3]

Baumeister P., 1994, European Patent, Patent No. [EP584043, 584043]

[4]

Beller M., 2004, TRANSITION METALS OR

[5] Supported palladium catalysts for fine chemicals synthesis [J].

Blaser, HU ;

Indolese, A ;

Schnyder, A ;

Steiner, H ;

Studer, M .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2001, 173 (1-2) :3-18

[6] Selective Semihydrogenation of Alkynes with N-Graphitic-Modified Cobalt Nanoparticles Supported on Silica [J].

Chen, Feng ;

Kreyenschulte, Carsten ;

Radnik, Joerg ;

Lund, Henrik ;

Surkus, Annette-Enrica ;

Junge, Kathrin ;

Beller, Matthias .

ACS CATALYSIS, 2017, 7 (03) :1526-1532

[7] Identifying active sites of CoNC/CNT from pyrolysis of molecularly defined complexes for oxidative esterification and hydrogenation reactions [J].

Cheng, Tianyuan ;

Yu, Hao ;

Peng, Feng ;

Wang, Hongjuan ;

Zhang, Bingsen ;

Su, Dangsheng .

CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (04) :1007-1015

[8] The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].

Chinchilla, Rafael ;

Najera, Carmen .

CHEMICAL REVIEWS, 2007, 107 (03) :874-922

[9] Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals [J].

Climent, Maria J. ;

Corma, Avelino ;

Iborra, Sara .

CHEMICAL REVIEWS, 2011, 111 (02) :1072-1133

[10] Molecular Adsorbates Switch on Heterogeneous Catalysis: Induction of Reactivity by N-Heterocyclic Carbenes [J].

Ernst, Johannes B. ;

Schwermann, Christian ;

Yokota, Gen-Ichi ;

Tada, Mizuki ;

Muratsugu, Satoshi ;

Doltsinis, Nikos L. ;

Glorius, Frank .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (27) :9144-9147

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