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

被引：58

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 [J].

Abe, H ;

Takeda, S ;

Takeuchi, Y ;

Harayama, T .

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 [J].

ADAM, W ;

SAUTER, M .

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 [J].

AMATORE, C ;

BLART, E ;

GENET, JP ;

JUTAND, A ;

LEMAIREAUDOIRE, S ;

SAVIGNAC, M .

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 [J].

Ashraf, MA ;

Jones, MA ;

Kelly, NE ;

Mullaney, A ;

Snaith, JS ;

Williams, I .

TETRAHEDRON LETTERS, 2003, 44 (15) :3151-3154

[7] Poly(N-isopropylacrylamide) soluble polymer supports in catalysis and synthesis [J].

Bergbreiter, DE ;

Case, BL ;

Liu, YS ;

Caraway, JW .

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 [J].

Botana, E ;

Nättinen, K ;

Prados, P ;

Rissanen, K ;

de Mendoza, J .

ORGANIC LETTERS, 2004, 6 (07) :1091-1094

[9] INTRAMOLECULAR [2+2] CYCLOADDITIONS OF KETENES TO CARBONYL GROUPS - A NOVEL SYNTHESIS OF SUBSTITUTED BENZOFURANS [J].

BRADY, WT ;

GIANG, YSF ;

MARCHAND, AP ;

WU, AH .

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 [J].

Bringmann, G ;

Tasler, S .

TETRAHEDRON, 2001, 57 (02) :331-343

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