Methodology for the synthesis of 1,2-disubstituted arylnaphthalenes from α-tetralones

被引：37

作者：

Moleele, SS ^{[1
]}

Michael, JP ^{[1
]}

de Koning, CB ^{[1
]}

机构：

[1] Univ Witwatersrand, Inst Mol Sci, Sch Chem, ZA-2050 Wits, South Africa

来源：

TETRAHEDRON | 2006年 / 62卷 / 12期

基金：

新加坡国家研究基金会; 美国安德鲁·梅隆基金会;

关键词：

Suzuki-Miyaura coupling reactions; aromatization; arylnaphthalenes; alpha-tetralone;

D O I：

10.1016/j.tet.2006.01.013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Tetralones were initially converted into 1-bromo-dihydronaphthalene-2-carbaldehydes and 1-bromo-naphthalene-2carbaldehydes. These precursors were then subjected to Suzuki coupling reactions to afford 1,2-disubstituted aryldihydronaphthalenes and 1,2-disubstituted arylnaphthalenes, respectively. The former products were oxidized with DDQ to give 1,2-disubstituted arylnaphthalenes. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：2831 / 2844

页数：14

共 10 条

[1] Atroposelective synthesis of axially chiral biaryl compounds [J].

Bringmann, G ;

Mortimer, AJP ;

Keller, PA ;

Gresser, MJ ;

Garner, J ;

Breuning, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5384-5427

[2] A new class of high affinity thyromimetics containing a phenyl-naphthylene core [J].

Hangeland, JJ ;

Friends, TJ ;

Doweyko, AM ;

Mellström, K ;

Sandberg, J ;

Grynfarb, M ;

Ryono, DE .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (20) :4579-4584

[3] Highly enantioselective catalytic conjugate additions to cyclohexadienones [J].

Imbos, R ;

Brilman, MHG ;

Pineschi, M ;

Feringa, BL .

ORGANIC LETTERS, 1999, 1 (04) :623-625

[4] The synthesis of (S)-(+)-gossypol via an asymmetric Ullmann coupling [J].

Meyers, AI ;

Willemsen, JJ .

CHEMICAL COMMUNICATIONS, 1997, (16) :1573-1574

[5] Synthesis of a resveratrol analogue with high ceramide-mediated proapoptotic activity on human breast cancer cells [J].

Minutolo, F ;

Sala, G ;

Bagnacani, A ;

Bertini, S ;

Carboni, I ;

Placanica, G ;

Prota, G ;

Rapposelli, S ;

Sacchi, N ;

Macchia, M ;

Ghidoni, R .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (22) :6783-6786

[6] Metal-ligand bifunctional catalysis: A nonclassical mechanism for asymmetric hydrogen transfer between alcohols and carbonyl compounds [J].

Noyori, R ;

Yamakawa, M ;

Hashiguchi, S .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :7931-7944

[7]

Noyori R, 2001, ANGEW CHEM INT EDIT, V40, P40, DOI 10.1002/1521-3773(20010105)40:1<40::AID-ANIE40>3.0.CO

[8]

2-5

[9] Recent progress in asymmetric two-center catalysis [J].

Shibasaki, M ;

Kanai, M ;

Funabashi, K .

CHEMICAL COMMUNICATIONS, 2002, (18) :1989-1999

[10] Lanthanide complexes in multifunctional asymmetric catalysis [J].

Shibasaki, M ;

Yoshikawa, N .

CHEMICAL REVIEWS, 2002, 102 (06) :2187-2209

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