Palladium-catalyzed, sequential, three-component cross-coupling of aryl halides, alkynes, and arynes

被引:130
作者
Liu, Zhijian [1 ]
Larock, Richard C. [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
关键词
alkynes; arynes; cross-coupling; palladium; polycycles;
D O I
10.1002/anie.200604969
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Three's a crowd? Polycyclic aromatic hydrocarbons can be synthesized efficiently and in high yield using the first palladium-catalyzed, sequential, three-component coupling of alkynes and arynes with aryl halides (see scheme). This process appears to involve the catalytic, stepwise carbopalladation of an alkyne and an aryne to generate the three-component products. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2535 / 2538
页数:4
相关论文
共 32 条
[1]  
[Anonymous], ANGEW CHEM
[2]   GROUP-4 METAL-COMPLEXES OF BENZYNES, CYCLOALKYNES, ACYCLIC ALKYNES, AND ALKENES [J].
BUCHWALD, SL ;
NIELSEN, RB .
CHEMICAL REVIEWS, 1988, 88 (07) :1047-1058
[3]   A combined zirconocene benzyne-palladium cross-coupling route to substituted biphenyls and terphenyls [J].
Frid, M ;
Pérez, D ;
Peat, AJ ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (40) :9469-9470
[4]   Three-component coupling of benzyne: Domino intermolecular carbopalladation [J].
Henderson, Jaclyn L. ;
Edwards, Andrew S. ;
Greaney, Michael F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) :7426-7427
[5]   Palladium-catalyzed carbopalladation and carbocyclization of arynes with aryl halides: a highly efficient route to functionalized triphenylenes [J].
Jayanth, TT ;
Cheng, CH .
CHEMICAL COMMUNICATIONS, 2006, (08) :894-896
[6]   Highly efficient route to o-allylbiaryls via palladium-catalyzed three-component coupling of benzynes, allylic halides, and aryl organometallic reagents [J].
Jayanth, TT ;
Jeganmohan, M ;
Cheng, CH .
ORGANIC LETTERS, 2005, 7 (14) :2921-2924
[7]   Palladium-catalyzed allylalkynylation of benzynes: A highly efficient route to substituted 1-allyl-2 alkynylbenzenes [J].
Jeganmohan, M ;
Cheng, CH .
ORGANIC LETTERS, 2004, 6 (16) :2821-2824
[8]   Synthesis of tetrasubstituted naphthalenes by palladium-catalyzed reaction of aryl iodides with internal alkynes [J].
Kawasaki, S ;
Satoh, T ;
Miura, M ;
Nomura, M .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) :6836-6838
[9]  
Kessar S.V., 1991, COMPREHENSIVE ORGANI, V4, P483
[10]   THE REACTIONS OF ALPHA-ALKOXY-SUBSTITUTED STYRENES WITH DIMETHYL ACETYLENEDICARBOXYLATE AND DIMETHYL FUMARATE NOVEL ADDUCTS IN THE REACTION WITH DIMETHYL FUMARATE [J].
KOTSUKI, H ;
YAMAGUCHI, T ;
OHNO, K ;
ICHIKAWA, Y ;
OCHI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (02) :599-602