Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation:: synthesis of benzo[b]furans and benzo[b]thiophenes

被引：86

作者：

Willis, Michael C. ^{[1
]}

Taylor, Dawn

Gillmore, Adam T.

机构：

[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England

[2] Pfizer Global Res & Dev, Chem Res & Dev Dept, Sandwich CT13 9NJ, Kent, England

来源：

TETRAHEDRON | 2006年 / 62卷 / 49期

基金：

英国工程与自然科学研究理事会;

关键词：

benzofuran; benzothiophene; palladium catalysis; enolate;

D O I：

10.1016/j.tet.2006.05.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enolates derived from alpha-(ortho-haloaryl)-substituted ketones undergo palladium-catalysed C-O bond formation to deliver benzofuran products in good yield. A catalyst generated from Pd-2(dba)(3) and the ligand DPEphos effects the key bond formation to deliver a variety of substituted products from both cyclic and acyclic precursors. The analogous thio-ketones undergo C-S bond formation using identical reaction conditions and are converted to benzothiophene products. A cascade sequence that produces the required a-aryl ketones in situ has also been developed, although the substrate scope is more restricted. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：11513 / 11520

页数：8

共 35 条

[1] Palladium-catalyzed intramolecular O-arylation of enolates:: Application to benzo[b]furan synthesis
Willis, MC
Taylor, D
Gillmore, AT
[J]. ORGANIC LETTERS, 2004, 6 (25) : 4755 - 4757
[2] Benzo[b]furan synthesis via palladium-catailysed intramolecular o-arylation of enolates.
Taylor, D
Willis, MC
Gillmore, AT
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U343 - U344
[3] Synthesis of Benzo-fused Heterocycles by Intramolecular α-Arylation of Ketone Enolate Anions
Guastavino, Javier F.
Rossi, Roberto A.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01): : 460 - 472
[4] Palladium-catalysed direct synthesis of benzo[b]thiophenes from thioenols
Inamoto, Kiyofumi
Arai, Yukari
Hiroya, Kou
Doi, Takayuki
[J]. CHEMICAL COMMUNICATIONS, 2008, (43) : 5529 - 5531
[5] A concerted synthesis of hydroxychalcones, flavanones and benzo[b]furans through palladium-catalysed reactions
De, M
Majumdar, DP
Kundu, NG
[J]. JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1999, 76 (11-12) : 665 - 674
[6] Intramolecular palladium-catalysed enolate arylation of 2-and 3-iodoindole derivatives for the synthesis of β-carbolines, γ-carbolines, and pyrrolo[3,4-b]indoles
Sole, Daniel
Bennasar, M. -Lluisa
Jimenez, Ivan
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (12) : 4535 - 4544
[7] Palladium-catalysed intramolecular annulation of 2-haloanilines and ketones:: enolate arylation vs. nucleophilic addition to the carbonyl group
Solé, D
Vallverdú, L
Peidró, E
Bonjoch, J
[J]. CHEMICAL COMMUNICATIONS, 2001, (18) : 1888 - 1889
[8] Copper-catalysed intramolecular O-arylation of aryl chlorides and bromides:: a straightforward approach to benzo[d]oxazoles in water
Barbero, Nekane
Carril, Monica
SanMartin, Raul
Dominguez, Esther
[J]. TETRAHEDRON, 2007, 63 (42) : 10425 - 10432
[9] One-Pot Synthesis of Functionalized Benzo[b]thiophenes and Their Hetero-Fused Analogues via Intramolecular Copper-Catalyzed S-Arylation of In Situ Generated Enethiolates
Acharya, Anand
Kumar, S. Vijay
Saraiah, B.
Ila, H.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (05): : 2884 - 2892
[10] Scalable, Transition-Metal-Free Direct Oxime O-Arylation: Rapid Access to O-Arylhydroxylamines and Substituted Benzo[b]furans
Gao, Hongyin
Xu, Qing-Long
Keene, Craig
Kuerti, Laszlo
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (29) : 8883 - 8887

← 1 2 3 4 →