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Fe-Catalyzed Intramolecular Cross-Dehydrogenative Arylation (CDA), Efficient Synthesis of 1-Arylnaphthalenes and 4-Arylcoumarins
Helvetica Chimica Acta ( IF 1.8 ) Pub Date : 2021-06-10 , DOI: 10.1002/hlca.202100056
Feng Liu 1 , Haiyan Diao 2 , Changcheng wang 3 , Zhen Zhang 2 , Zhangjie Shi 3
Affiliation  

Direct cross-dehydrogenative coupling of different inert C−H bonds is the most straightforward and environmentally benign method to construct C−C bonds. In this paper, we developed an iron-catalyzed intramolecular cross-dehydrogenative arylation (CDA) between benzylic C(sp3)H bond and aromatic C(sp2)H bond. From the readily available linear substrates, 1-arylnaphthalenes and 4-arylcoumarins can be quickly constructed with moderate to good yield (18 examples, up to 73 % yield) in one step. Both symmetrical and unsymmetrical substrates with different functional groups could tolerate this system well to form the anticipated products. A radical initiated dehydrogenative cyclization-dehydrogenation tandem process was proposed.

中文翻译:

Fe催化的分子内交叉脱氢芳基化(CDA),1-芳基萘和4-芳基香豆素的有效合成

不同惰性 C-H 键的直接交叉脱氢偶联是构建 C-C 键的最直接和环境友好的方法。在本文中,我们开发了一种铁催化的苄基 C( sp 3 )H 键和芳族 C( sp 2 )H 键之间的分子内交叉脱氢芳基化 (CDA) 。从容易获得的线性底物,可以一步快速构建 1-芳基萘和 4-芳基香豆素,产率中等至良好(18 个例子,产率高达 73%)。具有不同官能团的对称和不对称底物都可以很好地耐受该系统以形成预期的产品。提出了自由基引发的脱氢环化-脱氢串联工艺。
更新日期:2021-07-16
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