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
作者:Guijie Li、Erjuan Wang、Haoyi Chen、Hongfeng Li、Yuanhong Liu、Peng George Wang
DOI:10.1016/j.tet.2008.07.021
日期:2008.9
A general and efficient synthesis of fluorenes or heterocycle-fused indenes including 3-thia-cyclopenta[a]indenes, 9-thia-indeno[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
芴或杂环稠合的茚基的一般有效合成方法,包括3-噻吩环戊[ a ]茚,9-噻吩[1,2- a ]茚,5,6-二氢茚并[ 2,1- b ]吲哚已经被开发出来。这种方法是由涉及的第一制备多步协议实现邻-formylbiaryls通过铃木-宫浦耦合的ø-溴苯甲醛与芳基硼酸的结合或芳基卤化物与2-甲酰基苯硼酸的偶联,然后进行Brignard加成反应或Lewis酸催化的Friedel-Crafts环化反应,形成所需的芴或茚环。该方法具有许多优点,例如产率高,选择性高,反应条件温和,起始原料容易获得等。
Highly efficient synthesis of polysubstituted fluorene via iron-catalyzed intramolecular Friedel–Crafts alkylation of biaryl alcohols
作者:Soumen Sarkar、Sukhendu Maiti、Krishnendu Bera、Swapnadeep Jalal、Umasish Jana
DOI:10.1016/j.tetlet.2012.08.005
日期:2012.10
An efficient and mild Fe(III)-catalyzed intramolecular Friedel–Crafts alkylation of biaryl methanol derivatives has been developed to achieve the substituted fluorenederivatives. The present reaction provides an excellent alternative to published methods because of its high yields, operational simplicity, mild conditions, and use of inexpensive and sustainable catalyst.