Preparation of Functionalized Organoindium Reagents by Means of Magnesium Insertion into Organic Halides in the Presence of InCl3 at Room Temperature

被引:29
作者
Bernhardt, Sebastian [1 ]
Shen, Zhi-Liang [1 ]
Knochel, Paul [1 ]
机构
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
基金
欧洲研究理事会;
关键词
cross-coupling; indium; insertion; magnesium; palladium; CROSS-COUPLING REACTIONS; LICL-MEDIATED PREPARATION; INDIUM ORGANOMETALLICS; TRIORGANOINDIUM REAGENTS; ARYLINDIUM REAGENTS; CATALYZED-REACTIONS; CARBON-CARBON; ARYL; ZINC; ALUMINUM;
D O I
10.1002/chem.201203795
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Magnesium, indium, palladium: An efficient one-pot procedure for the direct preparation of triorganoindium reagents from organic halides by means of magnesium insertion in the presence of InCl3 and LiCl is reported (see scheme). The organoindium reagents are obtained in good yields from functionalized aryl, heteroaryl, and alkyl bromides and benzyl chlorides at 25 °C in THF within 4h. Moreover, the resulting organoindium reagents could be efficiently used as reagents in Pd-catalyzed cross-coupling reactions with a wide functional group tolerance. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:828 / 833
页数:6
相关论文
共 58 条
[1]   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
[2]   Pd-catalyzed Suzuki-Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands [J].
Altman, Ryan A. ;
Buchwald, Stephen L. .
NATURE PROTOCOLS, 2007, 2 (12) :3115-3121
[3]  
Araki S., 2007, Comprehensive Organometallic Chemistry III, V9, P649, DOI DOI 10.1016/B0-08-045047-4/00122-9
[4]   Recent advances in indium-promoted organic reactions [J].
Auge, Jacques ;
Lubin-Germain, Nadege ;
Uziel, Jacques .
SYNTHESIS-STUTTGART, 2007, (12) :1739-1764
[5]   Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].
Barder, TE ;
Walker, SD ;
Martinelli, JR ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696
[6]  
Blümke T, 2010, NAT CHEM, V2, P313, DOI [10.1038/NCHEM.590, 10.1038/nchem.590]
[7]   InCl3-Catalyzed Synthesis of 1,2-Dimetallic Compounds by Direct Insertion of Aluminum or Zinc Powder [J].
Bluemke, Tobias D. ;
Klatt, Thomas ;
Koszinowski, Konrad ;
Knochel, Paul .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (39) :9926-9930
[8]   New Preparation of Benzylic Aluminum and Zinc Organometallics by Direct Insertion of Aluminum Powder [J].
Bluemke, Tobias D. ;
Groll, Klaus ;
Karaghiosoff, Konstantin ;
Knochel, Paul .
ORGANIC LETTERS, 2011, 13 (24) :6440-6443
[9]   Preparation of highly functionalized alkylzinc halides from alkyl bromides using Mg, ZnCl2 and LiCl [J].
Bluemke, Tobias D. ;
Piller, Fabian M. ;
Knochel, Paul .
CHEMICAL COMMUNICATIONS, 2010, 46 (23) :4082-4084
[10]  
Blumke T. D., 2012, ANGEW CHEM, V124, P10064