LiCl-Mediated Preparation of Functionalized Benzylic Indium(III) Halides and Highly Chemoselective Palladium-Catalyzed Cross-Coupling in a Protic Cosolvent

被引:79
作者
Chen, Yi-Hung [1 ]
Sun, Mai [1 ]
Knochel, Paul [1 ]
机构
[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
基金
欧洲研究理事会;
关键词
biaryls; cross-coupling; organoindium reagents; palladium; REAGENTS; ARYL; ORGANOMETALLICS; COMPLEXES; LIGANDS; ACCESS; ALLYL;
D O I
10.1002/anie.200805588
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Sensitive functional groups such as COR, CHO, or CH2OH can be present in benzylic indium reagents prepared by the direct insertion of indium in the presence of LiCl. These reagents undergo palladium-catalyzed cross-coupling reactions in the presence of a protic cosolvent after activation with iPrMgCl·LiCl (see scheme). Remarkable chemoselectivities are achieved by using various electrophiles containing NH or OH groups. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2236 / 2239
页数:4
相关论文
共 59 条
[1]  
ARAKI S, 2007, COMPREHENSIVE ORGANO, V9, P650
[2]   Recent advances in indium-promoted organic reactions [J].
Auge, Jacques ;
Lubin-Germain, Nadege ;
Uziel, Jacques .
SYNTHESIS-STUTTGART, 2007, (12) :1739-1764
[3]   Rationale behind the resistance of dialkylbiaryl phosphines toward oxidation by molecular oxygen [J].
Barder, Timothy E. ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (16) :5096-5101
[4]   Electronic effects on the selectivity of Pd-catalyzed C-N bond-forming reactions using biarylphosphine ligands: The competitive roles of amine binding and acidity [J].
Biscoe, Mark R. ;
Barder, Timothy E. ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (38) :7232-7235
[5]  
BISCOE MR, 2007, ANGEW CHEM, V4119, P7370
[6]   EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].
BORDWELL, FG .
ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463
[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]  
Chen H., 2008, ANGEW CHEM, V120, P7760
[9]   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
[10]  
CHUPAK LS, 2008, J ORG CHEM