Iron(III) chloride in oxidative C-C coupling reactions

被引:416
作者
Sarhan, Abdelwareth A. O. [1 ]
Bolm, Carsten [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
关键词
HEXA-PERI-HEXABENZOCORONENE; POLYCYCLIC AROMATIC-HYDROCARBONS; RAY CRYSTAL-STRUCTURE; INTRAMOLECULAR SCHOLL REACTION; SUBSTITUTED TRIPHENYLENES; ORGANIC-SYNTHESIS; SOLID-STATE; CHEMICAL POLYMERIZATION; ELECTRONIC-PROPERTIES; CATALYTIC-SYSTEM;
D O I
10.1039/b906026j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this critical review, the use of iron(III) chloride in oxidative C-C couplings of arenes and related unsaturated compounds is presented and reviewed. The approach allows highly selective dimerisations of phenol derivatives, naphthols, and heterocyclic compounds. Sequential couplings give access to structurally well-defined oligo-and polymers. Iron(III) chloride is commercially available and inexpensive. Being a mild oxidising agent it has been applied in numerous reactions leading to new carbon -carbon-bonds in complex molecular arrays (107 references).
引用
收藏
页码:2730 / 2744
页数:15
相关论文
共 119 条
[51]   Controlling the Scholl reaction [J].
King, Benjamin T. ;
Kroulik, Jiri ;
Robertson, Charles R. ;
Rempala, Pawel ;
Hilton, Cameron L. ;
Korinek, Justin D. ;
Gortari, Lisa M. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (07) :2279-2288
[52]   Unexpected Side Chain Oxidation in a Swivel Cruciform Oligothiophene [J].
Koenen, Jan-Moritz ;
Bilge, Askin ;
Allard, Sybille ;
Alle, Ronald ;
Meerholz, Klaus ;
Scherf, Ullrich .
ORGANIC LETTERS, 2009, 11 (10) :2149-2152
[53]   Direct oxidative cyclization of 1,2-bis(benzothiophene-2-yl)ethylenes as a replacement of photocyclization in the synthesis of thiaheterohelicenes [J].
Larsen, J ;
Bechgaard, K .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) :1151-1152
[54]  
LECLERC M, 1989, MAKROMOL CHEM, V190, P3105
[55]   Novel oxidative coupling of 2-naphthols to 1,1′-bi-2-naphthols catalysed by solid Lewis acids using atmospheric oxygen as oxidant [J].
Li, TS ;
Duan, HY ;
Li, BZ ;
Tewari, BB ;
Li, SH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (03) :291-293
[56]   Facile Optimal Synthesis of Inherently Electroconductive Polythiophene Nanoparticles [J].
Li, Xin-Gui ;
Li, Ji ;
Huang, Mei-Rong .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (26) :6446-6455
[57]   Semi-fused hexaphenyl hexa-peri-hexabenzocoronene: a novel fluorophore from an intramolecular Scholl reaction [J].
Lu, Yunyi ;
Moore, Jeffrey S. .
TETRAHEDRON LETTERS, 2009, 50 (28) :4071-4077
[58]  
MARTINEZ F, 1999, INT J POLYM MATER, V44, P265
[59]   MALDI-MS evaluation of poly(3-hexylthiophene) synthesized by chemical oxidation with FeCl3 [J].
McCarley, TD ;
Noble, CO ;
DuBois, CJ ;
McCarley, RL .
MACROMOLECULES, 2001, 34 (23) :7999-8004
[60]  
McCullough RD, 1998, ADV MATER, V10, P93, DOI 10.1002/(SICI)1521-4095(199801)10:2<93::AID-ADMA93>3.3.CO