Facile synthesis of 1,7,8-trifluoro-2-naphthol via DMAP catalyzed cycloaromatization

被引：10

作者：

Araki, Keisuke ^{[1
]}

Katagiri, Tomohiro ^{[2
]}

Inoue, Munenori ^{[1
]}

机构：

[1] Sagami Chem Res Inst, Ayase, Kanagawa 2521193, Japan

[2] Tokai Univ, Dept Appl Chem, Grad Sch Engn, Hiratsuka, Kanagawa 2591292, Japan

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2014年 / 157卷

关键词：

1,7,8-Trifluoro-2-naphthol; Liquid crystal compounds; Deoxyfluorination; Suzuki-Miyaura vinylation; Intramolecular cycloaromatization; SPECTRUM DEOXOFLUORINATING AGENT; CROSS-COUPLING REACTIONS; BIS(2-METHOXYETHYL)AMINOSULFUR TRIFLUORIDE; KEDARCIDIN CHROMOPHORE; ARYL;

D O I：

10.1016/j.jfluchem.2013.11.005

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A facile synthesis of 1,7,8-trifluoro-2-naphthol, an important synthetic intermediate for liquid crystal compounds with a 1,7,8-trifluoronaphthalene structure, was developed starting from 4-bromo-1,2-difluorobenzene via DMAP catalyzed intramolecular cycloaromatization in 51% overall yield for the 6 steps. (C) 2013 Elsevier B.V. All rights reserved.

引用

页码：41 / 47

页数：7

共 37 条

[1] Enantioselective synthesis of nicotinic receptor probe 7,8-difluoro-1,2,3,4,5,6-hexahydro-1,5-methano-3-benzazocine [J].

Bashore, Crystal G. ;

Vetelino, Michael G. ;

Wirtz, Michael C. ;

Brooks, Paige R. ;

Frost, Heather N. ;

McDermott, Ruth E. ;

Whritenour, David C. ;

Ragan, John A. ;

Rutherford, Jennifer L. ;

Makowski, Teresa W. ;

Brenek, Steven J. ;

Coe, Jotham W. .

ORGANIC LETTERS, 2006, 8 (26) :5947-5950

[2] Aminodifluorosulfinium Tetrafluoroborate Salts as Stable and Crystalline Deoxofluorinating Reagents [J].

Beaulieu, Francis ;

Beauregard, Louis-Philippe ;

Courchesne, Gabriel ;

Couturier, Michel ;

LaFlamme, Francois ;

L'Heureux, Alexandre .

ORGANIC LETTERS, 2009, 11 (21) :5050-5053

[3] The TV in Your Pocket: Development of Liquid-Crystal Materials for the New Millennium [J].

Bremer, Matthias ;

Kirsch, Peer ;

Klasen-Memmer, Melanie ;

Tarumi, Kazuaki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (34) :8880-8896

[4] Potassium organotrifluoroborates: New perspectives in organic synthesis [J].

Darses, Sylvain ;

Genet, Jean-Pierre .

CHEMICAL REVIEWS, 2008, 108 (01) :288-325

[5] Palladium- (and nickel-) catalyzed vinylation of aryl halides [J].

Denmark, Scott E. ;

Butler, Christopher R. .

CHEMICAL COMMUNICATIONS, 2009, (01) :20-33

[6] BIOMIMETIC SYNTHESES OF PRETETRAMIDES .1. SYNTHESIS OF PRETETRAMIDE BY TANDEM EXTENSION OF A POLYKETIDE CHAIN [J].

GILBREATH, SG ;

HARRIS, CM ;

HARRIS, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6172-6179

[7] The fascinating influence of fluoro substituents on the synthesis and properties of liquid crystals [J].

Hird, M ;

Goodby, JW ;

Lewis, RA ;

Toyne, KJ .

MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2003, 401 :115-132

[8] Fluorinated liquid crystals - properties and applications [J].

Hird, Michael .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (12) :2070-2095

[9] Fluoro Substitution in Thermotropic Liquid Crystals [J].

Hird, Michael ;

Toyne, Kenneth J. .

MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1998, 323 :1-67

[10] Synthetic study of kedarcidin chromophore: Revised structure [J].

Kawata, S ;

Ashizawa, S ;

Hirama, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (49) :12012-12013

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