New efficient preparation of functionalized arylzinc or thienylzinc compounds from aryl or thienyl chlorides using cobalt catalysis

被引：43

作者：

Gosmini, C ^{[1
]}

Amatore, M ^{[1
]}

Claudel, S ^{[1
]}

Périchon, J ^{[1
]}

机构：

[1] Univ Paris 12, CNRS, UMR 7582, Lab Electrochim Catalyse & Synth Organ, F-94320 Thiais, France

来源：

SYNLETT | 2005年 / 14期

关键词：

cobalt halide; catalysis; zinc; thiophenes; aromatic chlorides;

D O I：

10.1055/s-2005-872250

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new chemical method is described for the preparation of aryl or thienyl zinc intermediates from their corresponding aromatic or thienyl chlorides in a mixture of acetonitrile-pyridine, using cobalt catalysis. This procedure allows for the synthesis of a variety of functionalized arylzinc species from reactive arylchlorides or chlorothiophenes in good to excellent yields. Some of these arylzinc compounds have been coupled with aromatic bromides using palladium catalysis.

引用

页码：2171 / 2174

页数：4

共 14 条

[1] Stability and reactivity of electrogenerated cobalt(I) towards aryl halides in the presence of additives such as vinyl acetate or methyl vinyl ketone -: Application to the electrosynthesis of arylzinc compounds
Buriez, O
Nédélec, JY
Périchon, J
[J]. JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2001, 506 (02): : 162 - 169
[2] New chemical synthesis of functionalized arylzinc compounds from aromatic or thienyl bromides under mild conditions using a simple cobalt catalyst and zinc dust
Fillon, H
Gosmini, C
Périchon, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (13) : 3867 - 3870
[3] Pure acetonitrile as solvent for the efficient electrochemical conversion of aryl bromides in organozinc species and their coupling reaction with acetyl chloride
Fillon, H
Le Gall, E
Gosmini, C
Périchon, J
[J]. TETRAHEDRON LETTERS, 2002, 43 (34) : 5941 - 5944
[4] Electrosynthesis of functionalized organodizinc compounds from aromatic dihalides via a cobalt catalysis in acetonitrile/pyridine as solvent
Fillon, H
Gosmini, C
Nédélec, JY
Périchon, J
[J]. TETRAHEDRON LETTERS, 2001, 42 (23) : 3843 - 3846
[5] Electrosynthesis of 3-thienylzinc bromide from 3-bromothiophene via a nickel catalysis.
Gosmini, C
Nedelec, JY
Perichon, J
[J]. TETRAHEDRON LETTERS, 1997, 38 (11) : 1941 - 1942
[6] New efficient preparation of arylzinc compounds from aryl halides using cobalt catalysis and sacrificial anode process
Gosmini, C
Rollin, Y
Nédélec, JY
Périchon, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) : 6024 - 6026
[7] Functionalized arylzinc compounds in ethereal solvent: Direct synthesis from aryl iodides and zinc powder and application to Pd-catalyzed reaction with allylic halides
Ikegami, R
Koresawa, A
Shibata, T
Takagi, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06) : 2195 - 2199
[8] New progress in the cobalt-catalysed synthesis of aromatic organozinc compounds by reduction of aromatic halides by zinc dust
Kazmierski, I
Gosmini, C
Paris, JM
Périchon, J
[J]. TETRAHEDRON LETTERS, 2003, 44 (34) : 6417 - 6420
[9] Nucleophilic catalysis of the iodine-zinc exchange reaction: Preparation of highly functionalized diaryl zinc compounds
Kneisel, FF
Dochnahl, M
Knochel, P
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (08) : 1017 - 1021
[10] A LiCl-mediated Br/Mg exchange reaction for the preparation of functionalized aryl- and heteroarylmagnesium compounds from organic bromides
Krasovskiy, A
Knochel, P
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (25) : 3333 - 3336

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