A general and efficient synthesis of substituted fluorenes and heterocycle-fused indenes containing thiophene or indole rings utilizing a Suzuki-Miyaura coupling and acid-catalyzed Friedel-Crafts reactions as key steps

被引：64

作者：

Li, Guijie ^{[1
]}

Wang, Erjuan ^{[2
]}

Chen, Haoyi ^{[1
]}

Li, Hongfeng ^{[2
]}

Liu, Yuanhong ^{[1
]}

Wang, Peng George ^{[3
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

[2] E China Normal Univ, Dept Chem, Shanghai 200062, Peoples R China

[3] Ohio State Univ, Dept Chem & Biochem, Columbus, OH 43210 USA

来源：

TETRAHEDRON | 2008年 / 64卷 / 38期

基金：

中国国家自然科学基金;

关键词：

Suzuki-Miyaura coupling; Friedel-Crafts cyclization; Bronsted acid catalysis; fluorenes; heteroarenes;

D O I：

10.1016/j.tet.2008.07.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and efficient synthesis of fluorenes or heterocycle-fused indenes including 3-thia-cyclopenta[a]indenes, 9-thia-indenol[1,2-a]indenes, 5,6-dihydroindeno[2,1-b]indoles has been developed. This methodology is realized by a multistep protocol. involving first preparation of ortho-formylbiaryls through Suzuki-Miyaura Coupling of o-bromobenzaldehydes with arylboronic acids or the coupling of aryl halides with 2-formylbenzene boronic acid, this is followed by Grignard addition and Friedel-Crafts cyclization reactions catalyzed by Bronsted or Lewis acid to form the desired fluorene or indene rings. The method offers several advantages such as high yields, high selectivities, mild reaction conditions, easily accessible starting materials, and so on. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：9033 / 9043

页数：11

共 2 条

[1] Synthesis of Biaryl Carboxylic Acids through a Cascade Suzuki-Miyaura Coupling/Friedel-Crafts Alkylation/Lewis-Acid-Catalyzed Rearrangement/Aromatization Process
Liu, Shaodong
Cheng, Liang
Liu, Li
ORGANIC LETTERS, 2024, 26 (09) : 1902 - 1907
[2] Synthesis of conformationally constrained α-amino acid derivatives containing bicyclo[2.2.2] unit via the Diels-Alder and Suzuki-Miyaura cross-coupling reactions as key steps
Kotha, Sambasivarao
Meshram, Milind
Muthusamy, Gopinathan
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2015, 54 (04): : 505 - 513

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