Regioselective diarylation of ketone enolates by homogeneous and heterogeneous catalysis:: synthesis of triarylethanones

被引：28

作者：

Churruca, F ^{[1
]}

SanMartin, R ^{[1
]}

Tellitu, I ^{[1
]}

Domínguez, E ^{[1
]}

机构：

[1] Euskal Herriko Unibertsitatea, Zientzi Fak, Kim Organ Saila 2, Bilbao 48080, Spain

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 31期

关键词：

arylation; ketones; palladium and compounds;

D O I：

10.1016/S0040-4039(03)01398-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel, one-step approach to 1,2,2-triarylethanones is achieved by an efficient palladium-catalyzed alpha,alpha-diarylation of commercially available acetophenones. After assaying an array of experimental conditions, two convenient procedures, which avoid ortho-arylation side reactions, are chosen to perform the target regioselective diarylation. The former protocol is based on the use of such a simple homogeneous system as Pd(OAc)(2)/PPh3/Cs2CO3, and the latter one employs a commercially available polymer-anchored catalyst. FibreCat(TM) 1026. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：5925 / 5929

页数：5

共 61 条

[1] Silica-supported imine palladacycles - recyclable catalysts for the Suzuki reaction?
Bedford, RB
Cazin, CSJ
Hursthouse, MB
Light, ME
Pike, KJ
Wimperis, S
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 633 (1-2) : 173 - 181
[2] Catalyst product separation techniques in Heck reaction
Bhanage, BM
Arai, M
[J]. CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 2001, 43 (03): : 315 - 344
[3] Access to well-defined heterogeneous catalytic systems via ring-opening metathesis polymerization (ROMP): Applications in palladium(II)-mediated coupling reactions
Buchmeiser, MR
Wurst, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) : 11101 - 11107
[4] Formylation of aryl halides catalyzed by a silica-supported phosphine palladium complex
Cai, MZ
Zhao, H
Zhou, J
Song, CS
[J]. SYNTHETIC COMMUNICATIONS, 2002, 32 (06) : 923 - 926
[5] Multiple arylations of aromatics via removable palladacycle scaffolds: polycyclic compounds and their way of formation
Catellani, M
Motti, E
Paterlini, L
Bocelli, G
Righi, L
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 580 (01) : 191 - 196
[6] Palladium-catalyzed arylation of ketone enolates:: An expeditious entry to tamoxifen-related 1,2,2-triarylethanones
Churruca, F
SanMartin, R
Tellitu, I
Domínguez, E
[J]. ORGANIC LETTERS, 2002, 4 (09) : 1591 - 1594
[7] Polymer-supported catalysis in synthetic organic chemistry
Clapham, B
Reger, TS
Janda, KD
[J]. TETRAHEDRON, 2001, 57 (22) : 4637 - 4662
[8] Cortés J, 2000, EUR J ORG CHEM, V2000, P239
[9] de la Torre G, 2001, ANGEW CHEM INT EDIT, V40, P2895, DOI 10.1002/1521-3773(20010803)40:15<2895::AID-ANIE2895>3.0.CO
[10] 2-#

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