Aryne, ortho-Quinone Methide, and ortho-Quinodimethane: Synthesis of Multisubstituted Arenes Using the Aromatic Reactive Intermediates

被引：149

作者：

Yoshida, Hiroto ^{[1
]}

Ohshita, Joji ^{[1
]}

Kunai, Atsutaka ^{[1
]}

机构：

[1] Hiroshima Univ, Grad Sch Engn, Dept Appl Chem, Higashihiroshima 7398527, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2010年 / 83卷 / 03期

关键词：

NICKEL-CATALYZED ACYLSTANNYLATION; FRIEDEL-CRAFTS ACYLATION; TANDEM ADDITION-REARRANGEMENT; INTRAMOLECULAR BIS-SILYLATION; CARBON TRIPLE BONDS; FACILE N-ARYLATION; ORGANIC-SYNTHESIS; O-QUINODIMETHANES; SIGMA-BONDS; STRAIGHTFORWARD SYNTHESIS;

D O I：

10.1246/bcsj.20090245

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A useful synthetic method for building up multisubstituted arenes of structural complexity and diversity by use of aromatic reactive intermediates is described. Regardless of the transient character arising from a highly strained carbon carbon triple bond, arynes have been found to undergo facile insertion into an element element sigma-bond and three-component coupling reactions. In addition, ortho-quinone methides and ortho-quinodimethanes have also been demonstrated to be convertible into multisubstituted arenes by utilizing their exo-dienyl moieties.

引用

页码：199 / 219

页数：21

共 114 条

[1] TRAPPING OF ORTHO-QUINODIMETHANE WITH PARA-QUINONES - SYNTHESIS OF TETRAHYDRO-1,4-ANTHEACENEDIONES [J].

ASKARI, S ;

LEE, S ;

PERKINS, RR ;

SCHEFFER, JR .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (12) :3526-3529

[2] REACTIONS OF ORGANIC HALIDES WITH R3MMR3 COMPOUNDS (M=SI,GE,SN) IN PRESENCE OF TETRAKIS(TRIARYLPHOSPHINE) PALLADIUM [J].

AZARIAN, D ;

DUA, SS ;

EABORN, C ;

WALTON, DRM .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 117 (03) :C55-C57

[3] Element-element addition to alkynes catalyzed by the group 10 metals [J].

Beletskaya, I ;

Moberg, C .

CHEMICAL REVIEWS, 1999, 99 (12) :3435-3461

[4] Element-element additions to unsaturated carbon-carbon bonds catalyzed by transition metal complexes [J].

Beletskaya, Irina ;

Moberg, Christina .

CHEMICAL REVIEWS, 2006, 106 (06) :2320-2354

[5] Thermally induced endo to exo isomerization in the o-xylylene complexes of zerovalent ruthenium and osmium, M(η6-C6Me6){η4-o-(CH2)2C6Me4} (M = Ru, Os) [J].

Bennett, MA ;

Bown, M ;

Byrnes, MJ .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 571 (01) :139-144

[6] METAL-COMPLEXES OF SMALL CYCLOALKYNES AND ARYNES [J].

BENNETT, MA ;

SCHWEMLEIN, HP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1989, 28 (10) :1296-1320

[7] The reactivity of complexes of nickel(0) and platinum(0) containing benzyne and related small-ring alkynes [J].

Bennett, MA ;

Wenger, E .

CHEMISCHE BERICHTE-RECUEIL, 1997, 130 (08) :1029-1042

[8]

BENNETT MA, 1988, OTGANOMETALLICS, V17, P3784

[9] Mononuclear and binuclear o-xylylene derivatives of Pd(II) [J].

Campora, J ;

Graiff, C ;

Palma, P ;

Carmona, E ;

Tiripicchio, A .

INORGANICA CHIMICA ACTA, 1998, 269 (01) :191-201

[10]

CAUBERE P, 1968, B SOC CHIM FR, P3008

← 1 2 3 4 5 6 7 8 9 10 →