Synthesis of Alkyl Indium Reagents by Using Unactivated Alkyl Chlorides and Their Applications in Palladium-Catalyzed Cross-Coupling Reactions with Aryl Halides

被引:37
作者
Chen, Bing-Zhi [1 ]
Zhi, Man-Ling [1 ]
Wang, Chuang-Xin [1 ]
Chu, Xue-Qiang [1 ]
Shen, Zhi-Liang [1 ]
Loh, Teck-Peng [1 ,2 ]
机构
[1] Nanjing Tech Univ, Jiangsu Natl Synerget Innovat Ctr Adv Mat, Sch Chem & Mol Engn, Inst Adv Synth, Nanjing 211816, Jiangsu, Peoples R China
[2] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
关键词
KETENE SILYL ACETALS; IN-SITU GENERATION; ORGANOINDIUM REAGENTS; AQUEOUS-MEDIA; TRIORGANOINDIUM REAGENTS; UNSATURATED HALIDES; ARYLINDIUM REAGENTS; DIRECT INSERTION; ACID-CHLORIDE; ONE-POT;
D O I
10.1021/acs.orglett.8b00441
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for the preparation of alkyl indium reagents by using unactivated and cheap alkyl chlorides as substrates in the presence of indium and LiI was developed. The thus-formed alkyl indium species effectively underwent palladium-catalyzed cross-coupling reactions with aryl halides with wide functional group tolerance.
引用
收藏
页码:1902 / 1905
页数:4
相关论文
共 55 条
[1]   Iron-catalyzed annulation reaction of arylindium reagents and alkynes to produce substituted naphthalenes [J].
Adak, Laksmikanta ;
Yoshikai, Naohiko .
TETRAHEDRON, 2012, 68 (26) :5167-5171
[2]   Cobalt-Catalyzed Preparation of Arylindium Reagents from Aryl and Heteroaryl Bromides [J].
Adak, Laksmikanta ;
Yoshikai, Naohiko .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (18) :7563-7568
[3]  
Araki S., 2007, COMPREHENSIVE ORGANO, V9, P649
[4]   Preparation of Functionalized Organoindium Reagents by Means of Magnesium Insertion into Organic Halides in the Presence of InCl3 at Room Temperature [J].
Bernhardt, Sebastian ;
Shen, Zhi-Liang ;
Knochel, Paul .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (03) :828-833
[5]  
Blümke T, 2010, NAT CHEM, V2, P313, DOI [10.1038/NCHEM.590, 10.1038/nchem.590]
[6]  
Bouissane L., 2009, ORG LETT, V11, P1285
[7]   Enantioselective nickel-catalyzed cross-coupling reactions of trialkynylindium reagents with racemic secondary benzyl bromides [J].
Caeiro, Jorge ;
Sestelo, Jose Perez ;
Sarandeses, Luis A. .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (02) :741-746
[8]   Preparation of aryl and heteroaryl indium(III) reagents by the direct insertion of indium in the presence of LiCl [J].
Chen, Yi-Hung ;
Knochel, Paid .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (40) :7648-7651
[9]   LiCl-Mediated Preparation of Functionalized Benzylic Indium(III) Halides and Highly Chemoselective Palladium-Catalyzed Cross-Coupling in a Protic Cosolvent [J].
Chen, Yi-Hung ;
Sun, Mai ;
Knochel, Paul .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (12) :2236-2239
[10]   Palladium-Catalyzed Cross-Coupling Reactions of Benzyl Indium Reagents with Aryl Iodides [J].
Chupak, Louis S. ;
Wolkowski, Joanna P. ;
Chantigny, Yves A. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) :1388-1390