Nickel-Catalyzed Tetramerization of Alkynes: Synthesis and Structure of Octatetraenes

被引：18

作者：

Wu, Tsun-Cheng ^{[1
]}

Chen, Jheng-Jhih ^{[1
]}

Wu, Yao-Ting ^{[1
]}

机构：

[1] Natl Cheng Kung Univ, Dept Chem, Tainan 70101, Taiwan

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 18期

关键词：

CARBON BOND FORMATION; CONJUGATED OLIGOMERS; CYCLOOCTATETRAENES; COMPLEXES; DIMERIZATION; DIYNES;

D O I：

10.1021/ol201814q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of a catalytic system comprised of NiBr2(dppe) and Zn, arylacetylenes undergo tetramerization to form linear octatetraenes, generally in good to excellent yields. The structure of the coupling products was verified by X-ray crystallography.

引用

页码：4794 / 4797

页数：4

共 41 条

[1]

[Anonymous], 1998, Electronic materials: the oligomer approach

[2] [2+2+2] cycloaddition reactions catalyzed by transition metal complexes [J].

Chopade, Pramod R. ;

Louie, Janis .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2307-2327

[3] Electric Field Poled Organic Electro-optic Materials: State of the Art and Future Prospects [J].

Dalton, Larry R. ;

Sullivan, Philip A. ;

Bale, Denise H. .

CHEMICAL REVIEWS, 2010, 110 (01) :25-55

[4]

Diederich F, 2005, ACETYLENE CHEMISTRY: CHEMISTRY, BIOLOGY AND MATERIAL SCIENCE, pV

[5] ORGANIC-CHEMISTRY OF SUBVALENT TRANSITION-METAL COMPLEXES .9. OXIDATIVE ADDITION OF NICKEL(0) COMPLEXES TO CARBON CARBON BONDS IN BIPHENYLENE - FORMATION OF NICKELOLE AND 1,2-DINICKELECIN INTERMEDIATES [J].

EISCH, JJ ;

PIOTROWSKI, AM ;

HAN, KI ;

KRUGER, C ;

TSAY, YH .

ORGANOMETALLICS, 1985, 4 (02) :224-231

[6] The transient titanocene(II): Direct synthesis from solvated titanium(II) chloride and cyclopentadienylsodium and ensuing interception with diphenylacetylene as 1,1-bis(cyclopentadienyl)-2,3,4,5-tetraphenyltitanacyclopentadiene [J].

Eisch, John J. ;

Adeosun, Adetenu A. ;

Birmingham, John M. .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2007, (01) :39-43

[7] Polyfunctionalized cage compounds by pericyclic domino processes of 4,5-dicyanopyridazine with dienes: Applications and limits [J].

Giomi, D ;

Nesi, R ;

Turchi, S ;

Mura, E .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (02) :360-364

[8] Selective dimerization of 1,6-diynes catalyzed by ionic liquid-supported nickel complexes in an ionic liquid/toluene biphasic system [J].

Goswami, Avijit ;

Ito, Taichi ;

Saino, Naoko ;

Kase, Kouki ;

Matsuno, Chikashi ;

Okamoto, Sentaro .

CHEMICAL COMMUNICATIONS, 2009, (04) :439-441

[9]

Haley M.M., 2006, CARBON RICH COMPOUND

[10] PREPARATION OF SUBSTITUTED 5-VINYLCYCLOHEXA-1,3-DIENES AND TRICYCLO[2.2.2.02,6]OCT-7-ENES [J].

HEIMBACH, P ;

PLONER, KJ ;

THOMEL, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (04) :276-&

← 1 2 3 4 5 →