Multiple arylations of aromatics via removable palladacycle scaffolds: polycyclic compounds and their way of formation

被引：16

作者：

Catellani, M

Motti, E

Paterlini, L

Bocelli, G

Righi, L

机构：

[1] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy

[2] CNR, Ctr Studio Strutturist Diffrattometr, I-43100 Parma, Italy

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1999年 / 580卷 / 01期

关键词：

arylation; C-H activation; palladacycles; polyaromatics;

D O I：

10.1016/S0022-328X(98)01138-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Palladium-promoted selective arylation of aromatic substrates can be achieved with aryl iodides or bromides in the presence of bicyclo[2.2.1]hept-2-ene. On the basis of isolation of products corresponding to multiple arylations, evidence is provided that the process occurs according to a complex sequence of steps, involving bicycloheptene insertion into arylpalladium bonds and its expulsion when steric hindrance is generated by the process. (C) 1999 Elsevier Science S.A. All rights reserved.

引用

页码：191 / 196

页数：6

共 27 条

[1] PALLADIUM-CATALYZED CYCLIZATION OF 2-SUBSTITUTED HALOGENOARENES BY DEHYDROHALOGENATION
AMES, DE
OPALKO, A
[J]. TETRAHEDRON, 1984, 40 (10) : 1919 - 1925
[2] SOME REACTIONS OF 3-HALOGENOCINNOLINES CATALYZED BY PALLADIUM COMPOUNDS
AMES, DE
BULL, D
[J]. TETRAHEDRON, 1982, 38 (03) : 383 - 387
[3] PALLADACYCLES AS EFFICIENT CATALYSTS FOR ARYL COUPLING REACTIONS
BELLER, M
FISCHER, H
HERRMANN, WA
OFELE, K
BROSSMER, C
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17): : 1848 - 1849
[4] REGIOSELECTIVE RING-OPENING OF A PALLADIUM(IV) ALKYLAROMATIC METALLACYCLE BY BENZYL GROUP MIGRATION FROM PALLADIUM TO THE AROMATIC CARBON AND X-RAY STRUCTURE OF THE RESULTING PALLADIUM(II) COMPLEX
BOCELLI, G
CATELLANI, M
GHELLI, S
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 458 (1-2) : C12 - C15
[5] CANTY AJ, 1995, COMPREHENSIVE ORGANO, V9, P272
[6] CARDENAS DJ, 1994, ANGEW CHEM INT EDIT, V33, P2445
[7] PALLADIUM-(II) AND PALLADIUM-(IV) COMPLEXES AS INTERMEDIATES IN CATALYTIC C-C BOND-FORMING REACTIONS
CATELLANI, M
CHIUSOLI, GP
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 346 (01) : C27 - C30
[8] CONFORMATIONAL EFFECTS IN ELEMENTARY STEPS IN CATALYTIC REACTIONS - OXIDATIVE ADDITION OF 3-BROMOPROP-1-ENE TO A PALLADIUM(II) METALLACYCLIC COMPLEX
CATELLANI, M
MANN, BE
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 390 (02) : 251 - 255
[9] A complex catalytic cycle leading to a regioselective synthesis of o,o'-disubstituted vinylarenes
Catellani, M
Frignani, F
Rangoni, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2): : 119 - 122
[10] PALLADIUM-CATALYZED SYNTHESIS OF 1,2,3,4,4A,12B-HEXAHYDRO-1,4-METHANOTRIPHENYLENES
CATELLANI, M
CHIUSOLI, GP
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 286 (01) : C13 - C16

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