Iron-Catalyzed Reductive Coupling of Nitroarenes with Olefins: Intermediate of Iron-Nitroso Complex

Song Heng; Yang Zhuoyi; Tung Chen-Ho; Wang Wenguang

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Iron-Catalyzed Reductive Coupling of Nitroarenes with Olefins: Intermediate of Iron-Nitroso Complex

机译：用烯烃的硝基甲烷的铁催化还原偶联：铁 - 硝基复合物中间体

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摘要

Using a single half-sandwich iron(II) compound, Cp*Fe(1,2-Ph2PC6H4S)(NCMe) (Cp*(-) = C5Me5-, 1) as a catalyst, reductive coupling of nitroarenes with olefins has been achieved by a well-defined iron(II)/(EtO)(3)SiH system. Through either inter- or intramolecular reductive coupling, various branched amines and indole derivatives have been directly synthesized in one-pot. Mechanistic studies showed that the catalysis is initiated by activation of nitroarenes by the iron(II) catalyst with silane, generating iron-nitrosoarene intermediate for the C-N bond coupling.

机译：使用单个半三明治铁（II）化合物，CP * Fe（1,2-PH2PC6H4S）（NCME）（CP *（ - ）= C5ME5-，1）作为催化剂，已经实现了Nitorenes与烯烃的还原偶联通过明确的铁（II）/（ETO）（3）SIH系统。通过间质或分子内还原偶联，各种支链胺和吲哚衍生物已直接在单罐中合成。机械研究表明，通过用硅烷的铁（II）催化剂激活硝基甲烷来引发催化，产生用于C-N键偶联的铁 - 亚硝基芳烃。

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来源
《ACS catalysis》 |2020年第1期|共6页
作者
Song Heng; Yang Zhuoyi; Tung Chen-Ho; Wang Wenguang;
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作者单位

Shandong Univ Key Lab Colloid &

Interface Chem Minist Educ Sch Chem &

Chem Engn 27 South Shanda Rd Jinan 250100 Peoples R China;

Shandong Univ Key Lab Colloid &

Interface Chem Minist Educ Sch Chem &

Chem Engn 27 South Shanda Rd Jinan 250100 Peoples R China;

Shandong Univ Key Lab Colloid &

Interface Chem Minist Educ Sch Chem &

Chem Engn 27 South Shanda Rd Jinan 250100 Peoples R China;

Shandong Univ Key Lab Colloid &

Interface Chem Minist Educ Sch Chem &

Chem Engn 27 South Shanda Rd Jinan 250100 Peoples R China;

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原文格式 PDF
正文语种 eng
中图分类物理化学（理论化学）、化学物理学;
关键词
reductive C-N bond coupling; iron catalysis; iron-nitrosoarene intermediate; secondary amines; indoles;

机译：还原C-N键偶联;铁催化;铁 - 亚硝基芳烃中间体;仲胺;吲哚;

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专利

1. Iron-Catalyzed Reductive Coupling of Nitroarenes with Olefins: Intermediate of Iron-Nitroso Complex [J] . Song Heng, Yang Zhuoyi, Tung Chen-Ho, ACS catalysis . 2020,第1期

机译：用烯烃的硝基甲烷的铁催化还原偶联：铁 - 硝基复合物中间体
2. Z-Selective Olefin Synthesis via Iron-Catalyzed Reductive Coupling of Alkyl Halides with Terminal Arylalkynes [J] . Chi Wai Cheung, Fedor E. Zhurkin, Xile Hu Journal of the American Chemical Society . 2015,第15期

机译：铁催化烷基卤化物与末端芳烃炔的Z选择性烯烃合成
3. Reduction of olefins, nitroarenes and Schiff base compounds by a polymer-supported [2-(2'-pyridyl)benzimidazole]palladium complex [J] . Shilpa M. L., Gayathri V. Transition Metal Chemistry . 2016,第4期

机译：通过聚合物负载的[2-（2'-吡啶基）苯并咪唑]钯配合物还原烯烃，硝基芳烃和席夫碱化合物
4. Iron-Catalyzed Intermolecular Addition of O-H Bond to Olefins [C] . Jun-Chul Choi, Kazufumi Kohno, Hiroyuki Yasuda Symposium on Organometallic Chemistry . 2007

机译：铁催化在烯烃中的O-H键的分子间添加
5. Mechanistic studies on enzymatic nitroarene reduction and implications for the fate of nitroarene mixtures in redox-stratified biofilm. [D] . Riefler, Roger Guy. 1999

机译：酶催化硝基芳烃还原的机理研究及其对氧化还原分层生物膜中硝基芳烃混合物的结局的影响。
6. Z-Selective Olefin Synthesisvia Iron-Catalyzed Reductive Coupling of Alkyl Halides with TerminalArylalkynes [O] . Chi Wai Cheung, Fedor E. Zhurkin, Xile Hu, -1

机译：Z-选择性烯烃合成通过铁催化烷基卤化物与末端的还原偶联芳炔
7. Iron-Catalyzed Reductive Coupling of Nitroarenes with Olefins: Intermediate of IronNitroso Complex [O] . -1

机译：用烯烃的铁催化硝基甲烷的还原偶联：Ironnitroso复合物中间体

Iron-Catalyzed Reductive Coupling of Nitroarenes with Olefins: Intermediate of Iron-Nitroso Complex

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