Synthesis of C3 Benzo[1,2-e:3,4-e':5,6-e"]tribenzo[l]acephenanthrylenes (Crushed fullerene derivatives) by intramolecular palladium-catalyzed arylation

被引：49

作者：

Gómez-Lor, B

González-Cantalapiedra, E

Ruiz, M

de Frutos, S

Cárdenas, DJ

Santos, A

Echavarren, AM

机构：

[1] Inst Ciencia Mat Madrid, Madrid 28049, Spain

[2] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain

[3] Lilly SA, Madrid 28018, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2004年 / 10卷 / 10期

关键词：

arylation; fullerenes; palladium; polyarenes; truxenes;

D O I：

10.1002/chem.200306023

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The C-60 polyarenes 4, 5, 18a, and 18b have been synthesized from truxene by triple alkylation at C5, C10, and C15 followed by a palladium-catalyzed intramolecular arylation. ne synthesis of "crushed fullerene" C60H30 (2) is the most efficient reported to date and proceeds in 33% overall yield.

引用

页码：2601 / 2608

页数：8

共 51 条

[11]

DEFRUTOS O, 1999, ANGEW CHEM, V111, P1552

[12]

DIEDERICH F, 1992, ANGEW CHEM, V104, P1123

[13] Palladium-catalyzed intramolecular arylation reaction:: Mechanism and application for the synthesis of polyarenes [J].

Echavarren, AM ;

Gómez-Lor, B ;

González, JJ ;

de Frutos, O .

SYNLETT, 2003, (05) :585-597

[14]

Faust R, 1998, ANGEW CHEM INT EDIT, V37, P2825, DOI 10.1002/(SICI)1521-3773(19981102)37:20<2825::AID-ANIE2825>3.0.CO

[15]

2-Y

[16] FULLERENE MODEL COMPOUNDS - BOWL-SHAPED AROMATIC-HYDROCARBONS AND CYCLOPHANE-BASED CAGE MOLECULES [J].

FAUST, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (13-14) :1429-1432

[17]

Faust R., 1998, ANGEW CHEM, V110, P2985

[18]

FAUST R, 1995, ANGEW CHEM, V107, P1559

[19] Zipping up 'the crushed fullerene' C60H30:: C60 by fifteen-fold, consecutive intramolecular H2 losses [J].

Gómez-Lor, B ;

Koper, C ;

Fokkens, RH ;

Vlietstra, EJ ;

Cleij, TJ ;

Jenneskens, LW ;

Nibbering, NMM ;

Echavarren, AM .

CHEMICAL COMMUNICATIONS, 2002, (04) :370-371

[20]

Gómez-Lor B, 2001, EUR J ORG CHEM, V2001, P2107

← 1 2 3 4 5 6 →