Synthesis of Substituted Naphthalenes via a Catalytic Ring-Expansion Rearrangement

被引：53

作者：

Glass, Adam C. ^{[1
]}

Morris, Benjamin B. ^{[1
]}

Zakharov, Lev N. ^{[1
]}

Liu, Shih-Yuan ^{[1
]}

机构：

[1] Univ Oregon, Dept Chem, Eugene, OR 97403 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 21期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1021/ol8019617

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new methodology for the preparation of substituted naphthalenes starting from readily available indenones, organometal reagents, and trimethylsilyldiazomethane via a catalytic rearrangement process is described. Hindered biaryl naphthalenes, including triortho-substituted biaryls, can be accessed through our method. Our results are consistent with a mechanism involving a benzobenzvalene intermediate.

引用

页码：4855 / 4857

页数：3

共 25 条

[1] AOYAMA T, 1989, CHEM PHARM BULL, V37, P253
[2] Regioselective synthesis of substituted naphthalenes:: A novel de novo approach based on a metal-free protocol for stepwise cycloaddition of o-alkynylbenzaldehyde derivatives with either alkynes or alkenes
Barluenga, J
Váquez-Villa, H
Ballesteros, A
González, JM
[J]. ORGANIC LETTERS, 2003, 5 (22) : 4121 - 4123
[3] BENZVALENE - PROPERTIES AND SYNTHETIC POTENTIAL
CHRISTL, M
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (6-7): : 529 - 546
[4] Modern methods for the synthesis of substituted naphthalenes
de Koning, CB
Rousseau, AL
van Otterlo, WAL
[J]. TETRAHEDRON, 2003, 59 (01) : 7 - 36
[5] DIEDERICH F, 2004, METAL CATALYZED CROS, P57167
[6] Annulation reactions of chromium carbene complexes:: scope, selectivity and recent developments
Dötz, KH
Tomuschat, P
[J]. CHEMICAL SOCIETY REVIEWS, 1999, 28 (03) : 187 - 198
[7] Tandem ring expansion of alkenyl benzocyclobutenol derivatives into substituted naphthols
Hamura, Toshiyuki
Suzuki, Takeaki
Matsumoto, Takashi
Suzuki, Keisuke
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (38) : 6294 - 6296
[8] Recent progress in selective additions of organometal reagents to carbonyl compounds
Hatano, Manabu
Miyamoto, Takashi
Ishihara, Kazuaki
[J]. CURRENT ORGANIC CHEMISTRY, 2007, 11 (02) : 127 - 157
[9] A novel synthesis of substituted naphthalenes via Claisen rearrangement and RCM reaction
Huang, KS
Wang, EC
[J]. TETRAHEDRON LETTERS, 2001, 42 (35) : 6155 - 6157
[10] Synthesis of substituted naphthalenes and carbazoles by the palladium-catalyzed annulation of internal alkynes
Huang, Q
Larock, RC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (19) : 7342 - 7349

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