Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction

Sun Peng; Yang Jiaojiao; Song Zirui; Cai Yichao; Liu Yajie; Chen Chunxia; Chen Xin; Peng Jinsong

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Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction

机译：铜介导通过顺序水醋酸化和交叉脱氢偶联反应的吲哚的单罐合成

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Starting from simple anilines and ester arylpropiolates, an efficient one-pot synthesis of 2-arylindole-3-carboxylate derivatives has been developed through copper-mediated sequential hydroamination and cross-dehydrogenative coupling (CDC) reaction. The initial hydroamination of anilines to ester arylpropiolates in benzene can proceed in a stereoselective manner to give ester (Z)-3-arylamino)acrylates in the presence of CuCl2/phenanthroline, KMnO4, and KHCO3 at 120 degrees C. Sequentially, these in situ functionalized adducts can undergo direct intramolecular oxidative alkenylation of aromatic C-H bond in mixed solvents (benzene/DMSO 1:1) at 130 degrees C affording multi-substituted indoles in good to high yields.

机译：从简单的苯胺和酯芳基丙二酸盐开始，通过铜介导的顺序的序贯水醋酸和交式脱氢偶联（CDC）反应，开发了一种有效的单罐合成2-芳基吲哚-3-羧酸酯衍生物。苯胺的初始水中对苯甲酸芳基甲磺酸盐的苯芳基醇酸盐可以以立体选择性方式进行，得到酯（Z）-3-芳基氨基）丙烯酸酯在CuCl 2 / PhenAnholine，KmnO 4和KhCO 3的存在下以120℃下依次，这些原位官能化加合物可以在130℃下在混合溶剂（苯/ DMSO 1：1）中进行直接的分子内氧化烯化酶，其在130℃下提供多取代的吲哚，其优于高产率。

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来源
《Synthesis: International Journal of Methods in Synthetic Organic Chemistry》 |2020年第1期|共10页
作者
Sun Peng; Yang Jiaojiao; Song Zirui; Cai Yichao; Liu Yajie; Chen Chunxia; Chen Xin; Peng Jinsong;
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作者单位

Northeast Forestry Univ Coll Chem Chem Engn &

Resource Utilizat 26 Hexing Rd Harbin 150040;

Northeast Forestry Univ Coll Chem Chem Engn &

Resource Utilizat 26 Hexing Rd Harbin 150040;

Northeast Forestry Univ Coll Chem Chem Engn &

Resource Utilizat 26 Hexing Rd Harbin 150040;

Northeast Forestry Univ Coll Chem Chem Engn &

Resource Utilizat 26 Hexing Rd Harbin 150040;

Northeast Forestry Univ Coll Chem Chem Engn &

Resource Utilizat 26 Hexing Rd Harbin 150040;

Northeast Forestry Univ Coll Chem Chem Engn &

Resource Utilizat 26 Hexing Rd Harbin 150040;

Northeast Forestry Univ Coll Chem Chem Engn &

Resource Utilizat 26 Hexing Rd Harbin 150040;

Northeast Forestry Univ Coll Chem Chem Engn &

Resource Utilizat 26 Hexing Rd Harbin 150040;

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正文语种 eng
中图分类化学;
关键词
copper-mediated; indoles; hydroamination; cross-dehydrogenative coupling; oxidation;

机译：铜介导;吲哚;氢化;交叉脱氢偶联;氧化;

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专利

1. Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction [J] . Sun Peng, Yang Jiaojiao, Song Zirui, Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2020,第1期

机译：铜介导通过顺序水醋酸化和交叉脱氢偶联反应的吲哚的单罐合成
2. Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan-Lam and cross-dehydrogenative coupling reactions [J] . Chen Xin, Bian Yunyun, Mo Baichuan, RSC Advances . 2020,第42期

机译：铜（II）通过顺序陈林和交叉脱氢偶联反应催化多异吲哚的合成
3. Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions [J] . Xin Chen, Yunyun Bian, Baichuan Mo, RSC Advances . 2020,第42期

机译：铜（II）通过顺序陈林和交叉脱氢偶联反应催化多异吲哚的合成
4. A CAN-catalyzed sequential three component reaction for the one-pot synthesis of tricyclic fused pyrrole systems [C] . Veronica Estevez, Mercedes Villacampa, J. Carlos Menendez European Symposium on Organic Chemistry . 2009

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5. I. Sequential carbon and sulfur coupling to dibromoalkenes. II. Effects of electron-withdrawing groups in the polarized Nazarov reaction. III. Progress towards the total synthesis of tetrapetalone A [D] . Herrick, Ildiko Rita 2008

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6. Sequential decarboxylative azide–alkyne cycloaddition and dehydrogenative coupling reactions: one-pot synthesis of polycyclic fused triazoles [O] . Kuppusamy Bharathimohan, Thanasekaran Ponpandian, A Jafar Ahamed, 2014

机译：顺序脱羧叠氮-炔环加成和脱氢偶联反应：多锅稠合三唑的一锅合成
7. Cu(OAc)2Promoted Oxidative Cross-Dehydrogenative Coupling Reaction of Acylmethyl Malonates with Indole Derivatives to Access 3Functionalized Indoles and Polycyclic Indoles [O] . -1

机译：Cu（OAC）2丙基甲基丙二酸酯与吲哚衍生物的氧化氧化脱氢偶联反应，以进入3个官能化吲哚和多环吲哚

Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction

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