A new, expeditious entry to the benzophenanthrofuran framework by a Pd-catalyzed C- and O-arylation/PIFA-mediated oxidative coupling sequence

被引：57

作者：

Churruca, F ^{[1
]}

SanMartin, R ^{[1
]}

Tellitu, I ^{[1
]}

Domínguez, E ^{[1
]}

机构：

[1] Euskal Herriko Unibertsitatea, Klim Organ Saila 2, Zientzia Teknol Fak, Bilbao, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 12期

关键词：

fused-ring systems; heterogeneous catalysis; oxidative coupling; oxygen heterocycles; palladium;

D O I：

10.1002/ejoc.200400856

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a series of 2,3-diarylbenzo[b]furans starting from 1,2-diarylethanones and 1,2-dibromoarenes proceeds by means of both homogeneous and polymer-anchored palladium catalysts. This tandem process can be effectively halted at the C-arylation step, thus providing key o-bromoarylated deoxybenzoin intermediates in good yields. The efficient oxidative coupling leading to benzo[b]phenanthro[9,10-d]furans is carried out using the safer hypervalent iodine reagent PIFA. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

引用

页码：2481 / 2490

页数：10

共 85 条

[1] An attempt for biaryl coupling reaction of benzyl benzoate derivatives under Ullmann conditions
Abe, H
Takeda, S
Takeuchi, Y
Harayama, T
[J]. HETEROCYCLES, 2003, 61 : 521 - +
[2] PHOTOCHEMICAL AND THERMAL REARRANGEMENT OF ACYL-SUBSTITUTED QUINONE METHIDES, ACCESSIBLE BY DIMETHYLDIOXIRANE OXIDATION OF BENZOFURANS AND SUBSEQUENT VALENCE ISOMERIZATION OF THE RESULTING EPOXIDES
ADAM, W
SAUTER, M
[J]. CHEMISCHE BERICHTE, 1993, 126 (12) : 2697 - 2699
[3] NEW SYNTHETIC APPLICATIONS OF WATER-SOLUBLE ACETATE PD/TPPTS CATALYST GENERATED IN-SITU - EVIDENCE FOR A TRUE PD(0) SPECIES INTERMEDIATE
AMATORE, C
BLART, E
GENET, JP
JUTAND, A
LEMAIREAUDOIRE, S
SAVIGNAC, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) : 6829 - 6839
[4] [Anonymous], METAL CATALYSED CROS
[5] ANTKOWIAK WZ, 1979, B ACAD POL SCI-CHIM, V27, P109
[6] Synthesis and photolysis studies of carboxylic esters of 2-hydroxy-1,2,2-triphenylethanone: a novel tandem photocyclisation
Ashraf, MA
Jones, MA
Kelly, NE
Mullaney, A
Snaith, JS
Williams, I
[J]. TETRAHEDRON LETTERS, 2003, 44 (15) : 3151 - 3154
[7] Poly(N-isopropylacrylamide) soluble polymer supports in catalysis and synthesis
Bergbreiter, DE
Case, BL
Liu, YS
Caraway, JW
[J]. MACROMOLECULES, 1998, 31 (18) : 6053 - 6062
[8] p-(1H-phenanthro[9,10-d]imidazol-2-yl)-substituted calix[4]arene, a deep cavity for guest inclusion
Botana, E
Nättinen, K
Prados, P
Rissanen, K
de Mendoza, J
[J]. ORGANIC LETTERS, 2004, 6 (07) : 1091 - 1094
[9] INTRAMOLECULAR [2+2] CYCLOADDITIONS OF KETENES TO CARBONYL GROUPS - A NOVEL SYNTHESIS OF SUBSTITUTED BENZOFURANS
BRADY, WT
GIANG, YSF
MARCHAND, AP
WU, AH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) : 3457 - 3461
[10] Oxidative aryl coupling reactions: a biomimetic approach to configurationally unstable or axially chiral biaryl natural products and related bioactive compounds
Bringmann, G
Tasler, S
[J]. TETRAHEDRON, 2001, 57 (02) : 331 - 343

← 1 2 3 4 5 6 7 8 9 →