A Direct Synthesis of Symmetrical (E,E)-1,4-Diaryl-1,3-butadienes by Wenkert Arylation of Thiophene

被引：15

作者：

Hintermann, Lukas ^{[1
]}

Schmitz, Marco ^{[2
]}

Chen, Yun ^{[2
]}

机构：

[1] Tech Univ Munich, Dept Chem, D-85747 Garching, Germany

[2] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 14-15期

关键词：

alkenes; cross-coupling; homogeneous catalysis; nickel; sulfur heterocycles; CARBON-CARBON BONDS; NICKEL-INDUCED CONVERSION; ONE-STEP TRANSFORMATIONS; STEREOSELECTIVE-SYNTHESIS; GRIGNARD-REAGENTS; EUDIA-PAVONIA; HECK REACTION; OLEFINS; OXYGEN; COMPLEXES;

D O I：

10.1002/adsc.201000350

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The nickel-catalyzed coupling of thiophene with aryl Grignard reagents (Wenkert reaction) is accelerated by N-heterocyclic carbene or trialkylphosphane ligands, providing a general, scalable direct synthesis of symmetrical 1,4-diarylbutadienes.

引用

页码：2411 / 2415

页数：5

共 50 条

[21] Chiral (E,E)-1,4-Dialkoxy-1,3-butadienes. - 1. Stereoselective Synthesis
Tetrahedron Lett, 39 (6921):
[22] Isomers and polymorphs of (E, E)-1,4-bis(nitro-phenyl)-2,3-diaza-1,3-butadienes
Glidewell, Christopher
Low, John N.
Skakle, Janet M. S.
Wardell, James L.
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2006, 62 (04): : 666 - 675
[23] Synthesis, pohtophysical, and computational studies of a series of 1,4-diaryl-1,3-butadiynes
Angelo, Michael San
Isovitsch, Ralph
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
[24] Stereoselective preparation of (E)- and (Z)-di- and trisubstituted 1,3-butadienes
Takeda, Takeshi
Tateishi, Keiichiro
Tsubouchi, Akira
TETRAHEDRON LETTERS, 2015, 56 (26) : 4016 - 4021
[25] Synthesis of highly substituted 1,3-butadienes by palladium-catalyzed arylation of internal alkynes
Satoh, T
Ogino, S
Miura, M
Aromitra, M
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (38) : 5063 - 5065
[26] SYNTHESIS OF 1,4-DISUBSTITUTED 2,3-DIMESITYL-1,3-BUTADIENES
LAGIDZE, RM
KUPRAVA, SD
VASHAKID.MS
SAMSONIY.GG
IREMADZE, NK
ZHURNAL ORGANICHESKOI KHIMII, 1972, 8 (08): : 1591 - &
[27] 1,3-CYCLOADDITION OF SUBSTITUTED BENZONITRILE OXIDES TO 1,4-DIARYL-1-AZA-1,3-BUTADIENES - A KINETIC-STUDY
CADONI, E
GELLI, G
BELTRAME, P
GAZZETTA CHIMICA ITALIANA, 1990, 120 (11): : 679 - 684
[28] A versatile synthesis of (E)- and (Z)-1-halo-2-(alkoxymethyl)-1,3-butadienes and their condensation with aldehydes
Wong, T
Tjepkema, MW
Audrain, H
Wilson, PD
Fallis, AG
TETRAHEDRON LETTERS, 1996, 37 (06) : 755 - 758
[29] SYNTHETIC EXPLOITATION OF THE RING-OPENING OF 3,4-DINITROTHIOPHENE - A NOVEL ACCESS TO 1,4-DIALKYL-2,3-DINITRO-1,3-BUTADIENES AND 1,4-DIARYL-2,3-DINITRO-1,3-BUTADIENES
DELLERBA, C
MELE, A
NOVI, M
PETRILLO, G
STAGNARO, P
TETRAHEDRON LETTERS, 1990, 31 (34) : 4933 - 4936
[30] Palladium-catalyzed trimerizations of terminal arylalkynes: Synthesis of 1,3-diaryl-2-arylethynyl-1,3-butadienes
Wu, Yao-Ting
Lin, Wei-Chih
Liu, Chia-Ju
Wu, Chuan-Yi
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (11-12) : 1841 - 1849

← 1 2 3 4 5 →