Preparation of Alkyl Indium Reagents by Iodine-Catalyzed Direct Indium Insertion and Their Applications in Cross-Coupling Reactions

Zhi Man-Ling; Chen Bin-Zhi; Deng Wei; Chu Xue-Qiang; Loh Teck-Peng; Shen Zhi-Liang

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Preparation of Alkyl Indium Reagents by Iodine-Catalyzed Direct Indium Insertion and Their Applications in Cross-Coupling Reactions

机译：通过碘催化直接铟插入制备烷基铟试剂及其在交叉偶联反应中的应用

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An efficient method for the synthesis of alkyl indium reagent by means of an iodine-catalyzed direct indium insertion into alkyl iodide in THF is reported. The thus-generated alkyl indium reagents effectively underwent Pd-catalyzed cross-coupling reactions with various aryl halides, exhibiting good compatibility to a variety of sensitive functional groups. By replacing THF with DMA and using 0.75 equiv of iodine, less reactive alkyl bromide could be used as substrate for indium insertion with equal ease.

机译：据报道，通过碘催化直接铟插入THF中烷基碘的烷基铟试剂合成烷基铟试剂的有效方法。由此产生的烷基铟试剂有效地介断了与各种芳基卤化物的PD催化的交联反应，对各种敏感官能团具有良好的相容性。通过用DMA替代THF并使用0.75当量的碘，可用较少的反应性烷基溴作为铟插入的基质，同等容易。

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来源
《The Journal of Organic Chemistry》 |2019年第5期|共7页
作者
Zhi Man-Ling; Chen Bin-Zhi; Deng Wei; Chu Xue-Qiang; Loh Teck-Peng; Shen Zhi-Liang;
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作者单位

Nanjing Tech Univ Inst Adv Synth Sch Chem &

Mol Engn Jiangsu Natl Synerget Innovat Ctr Adv Mat Nanjing 211816 Jiangsu Peoples R China;

Nanjing Tech Univ Inst Adv Synth Sch Chem &

Mol Engn Jiangsu Natl Synerget Innovat Ctr Adv Mat Nanjing 211816 Jiangsu Peoples R China;

Nanjing Tech Univ Inst Adv Synth Sch Chem &

Mol Engn Jiangsu Natl Synerget Innovat Ctr Adv Mat Nanjing 211816 Jiangsu Peoples R China;

Nanjing Tech Univ Inst Adv Synth Sch Chem &

Mol Engn Jiangsu Natl Synerget Innovat Ctr Adv Mat Nanjing 211816 Jiangsu Peoples R China;

Nanjing Tech Univ Inst Adv Synth Sch Chem &

Mol Engn Jiangsu Natl Synerget Innovat Ctr Adv Mat Nanjing 211816 Jiangsu Peoples R China;

Nanjing Tech Univ Inst Adv Synth Sch Chem &

Mol Engn Jiangsu Natl Synerget Innovat Ctr Adv Mat Nanjing 211816 Jiangsu Peoples R China;

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正文语种 eng
中图分类有机化学;
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1. Preparation of Alkyl Indium Reagents by Iodine-Catalyzed Direct Indium Insertion and Their Applications in Cross-Coupling Reactions [J] . Zhi Man-Ling, Chen Bin-Zhi, Deng Wei, The Journal of Organic Chemistry . 2019,第5期

机译：通过碘催化直接铟插入制备烷基铟试剂及其在交叉偶联反应中的应用
2. Synthesis of Alkyl Indium Reagents by Using Unactivated Alkyl Chlorides and Their Applications in Palladium-Catalyzed Cross-Coupling Reactions with Aryl Halides [J] . Bing-Zhi Chen, Man-Ling Zhi, Chuang-Xin Wang, Organic letters . 2018,第7期

机译：通过使用芳克催化芳基催化的烷基氯化物及其在钯催化的交叉偶联反应中的应用来合成烷基铟试剂
3. Preparation of Aryl and Heteroaryl Indium(III) Reagents by the Direct Insertion of Indium in the Presence of LiCl [J] . Yi-Hung Chen, Paul Knochel Angewandte Chemie . 2008,第40期

机译：在LiCl存在下直接插入铟制备芳基和杂芳基铟（III）试剂
4. Preparation of Allylic Indium(III)Reagents by Reductive Transmetalation of pi-Allypalladium(II)or pi-Allylnickel(II)with Indium(I)Iodide [C] . Tsunehisa Hirashita, Shinya Kambe, Shuki Araki Symposium on Organometallic Chemistry . 2003

机译：用铟（I）碘化物还原透射型（II）或Pi-烯丙基尼基（II）的制备烯丙基铟（III）试剂
5. Nickel-Catalyzed Cross-Coupling Reactions: Stereospecific Arylations, Formation of 2-PyridylZinc Reagents & Directed Hydroarylation of Alkynes [D] . Hanna, Luke Edward. 2016

机译：镍催化的交叉偶联反应：立体特异性芳族，形成2-吡啶基锌试剂和炔烃的指导水序列
6. Palladium-Catalyzed Reactions of Arylindium Reagents Prepared Directly from Aryl Iodides and Indium Metal [O] . Vardan Papoian, Thomas Minehan -1

机译：直接由芳基碘化物和铟金属制备的Arylindium试剂的钯催化反应
7. Palladium-Catalyzed Reactions of Arylindium Reagents Prepared Directly from Aryl Iodides and Indium Metal [O] . Vardan Papoian, Thomas Minehan 2008

机译：芳基试剂直接由芳基碘化物和铟金属制备的钯催化反应

Preparation of Alkyl Indium Reagents by Iodine-Catalyzed Direct Indium Insertion and Their Applications in Cross-Coupling Reactions

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