Cu-Based Nanoalloys in the Base-Free Ullmann Heterocyle-Aryl Ether Synthesis

被引：22

作者：

Engels, Volker ^{[1
]}

Benaskar, Faysal ^{[2
]}

Patil, Narendra ^{[2
]}

Rebrov, Evgeny V. ^{[2
]}

Hessel, Volker ^{[2
]}

Hulshof, Lumbertus A.

Jefferson, David A. ^{[1
]}

Vekemans, Jef A. J. M.

Karwal, Saurabh ^{[2
]}

Schouten, Jaap C. ^{[2
]}

Wheatley, Andrew E. H. ^{[1
]}

机构：

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

[2] Eindhoven Univ Technol, Lab Chem Reactor Engn, NL-5600 MB Eindhoven, Netherlands

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2010年 / 14卷 / 03期

关键词：

FOCUSED MICROWAVE IRRADIATION; NUCLEOPHILIC-SUBSTITUTION REACTIONS; COPPER NANOPARTICLES; DIARYL ETHERS; TERMINAL ALKYNES; METAL NANOPARTICLES; COUPLING REACTIONS; SUZUKI REACTIONS; CLICK CHEMISTRY; NANO-BRASS;

D O I：

10.1021/op9003423

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We report the first liquid-liquid Ullmann etherification process mediated not only by oxidatively stable Cu but also by CuZn and CuSn nanoparticle catalysts in conjunction with microwave heating that also avoids the use of solid and expensive bases. Conditions have led to improved turnovers and excellent yields in heteroaromatic Ullmann-type coupling reactions. Further enhancement is achieved upon the addition of 18-crown-6 as a kinetic promoter.

引用

页码：644 / 649

页数：6

共 58 条

[1] New synthetic methodologies based on active transition metals [J].

Alonso, Francisco ;

Yust, Miguel .

PURE AND APPLIED CHEMISTRY, 2008, 80 (05) :1005-1012

[2] Copper nanoparticles in click chemistry: an alternative catalytic system for the cycloaddition of terminal alkynes and azides [J].

Alonso, Francisco ;

Moglie, Yanina ;

Radivoy, Gabriel ;

Yus, Miguel .

TETRAHEDRON LETTERS, 2009, 50 (20) :2358-2362

[3]

[Anonymous], CHEM BER

[4] Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers [J].

Aranyos, A ;

Old, DW ;

Kiyomori, A ;

Wolfe, JP ;

Sadighi, JP ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4369-4378

[5] Copper(0) in the Ullmann heterocycle-aryl ether synthesis of 4-phenoxypyridine using multimode microwave heating [J].

Benaskar, Faysal ;

Engels, Volker ;

Patil, Narendra ;

Rebrov, Evgeny V. ;

Meuldijk, Jan ;

Hessel, Volker ;

Hulshof, Lumbertus A. ;

Jefferson, David A. ;

Schouten, Jaap C. ;

Wheatley, Andrew E. H. .

TETRAHEDRON LETTERS, 2010, 51 (02) :248-251

[6]

BHUSHAN B, 2007, SPRINGER HDB NANOTEC, pR44

[7] Heating of metallic powders by microwaves: Experiment and theory [J].

Buchelnikov, V. D. ;

Louzguine-Luzgin, D. V. ;

Xie, G. ;

Li, S. ;

Yoshikawa, N. ;

Sato, M. ;

Anzulevich, A. P. ;

Bychkov, I. V. ;

Inoue, A. .

JOURNAL OF APPLIED PHYSICS, 2008, 104 (11)

[8] Solution synthesis of nanocrystalline M-Zn (M = Pd, Au, Cu) intermetallic compounds via chemical conversion of metal nanoparticle precursors [J].

Cable, Robert E. ;

Schaak, Raymond E. .

CHEMISTRY OF MATERIALS, 2007, 19 (16) :4098-4104

[9] Copper bronze catalyzed Heck reaction in ionic liquids [J].

Calò, V ;

Nacci, A ;

Monopoli, A ;

Ieva, E ;

Cioffi, N .

ORGANIC LETTERS, 2005, 7 (04) :617-620

[10] Efficient nucleophilic substitution reactions of pyrimidyl and pyrazyl halides with nucleophiles, under focused microwave irradiation [J].

Cherng, YH .

TETRAHEDRON, 2002, 58 (05) :887-890

← 1 2 3 4 5 6 →