Two palladium-catalyzed domino reactions from one set of substrates/reagents:: Efficient synthesis of substituted indenes and cis-stilbenoid hydrocarbons from the same internal alkynes and hindered grignard reagents

被引:30
作者
Dong, Cheng-Guo [1 ]
Yeung, Pik
Hu, Qiao-Sheng
机构
[1] CUNY Coll Staten Isl, Dept Chem, Staten Isl, NY 10314 USA
[2] CUNY, Grad Ctr, Staten Isl, NY 10314 USA
关键词
D O I
10.1021/ol062885a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two types of domino reactions from the same internal alkynes and hindered Grignard reagents based on carbopalladation, Pd-catalyzed cross-coupling reaction, and a C-H activation strategy are described. The realization of these domino reactions relied on the control of the use of the ligand and the reaction temperature. Our study provides efficient access to useful polysubstituted indenes and cis-substituted stilbenes and may offer a new means of development of tandem/domino reactions in a more efficient way.
引用
收藏
页码:363 / 366
页数:4
相关论文
共 58 条
[1]   Palladium-assisted multicomponent synthesis of 2-aryl-4-aminoquinolines and 2-aryl-4-amino[1,8]naphthyridines [J].
Abbiati, G ;
Arcadi, A ;
Canevari, V ;
Capezzuto, L ;
Rossi, E .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6454-6460
[2]   Effect of the nature of metallocene complexes of group IV metals on their performance in catalytic ethylene and propylene polymerization [J].
Alt, HG ;
Köppl, A .
CHEMICAL REVIEWS, 2000, 100 (04) :1205-1221
[3]  
Barberá J, 1998, ANGEW CHEM INT EDIT, V37, P296, DOI 10.1002/(SICI)1521-3773(19980216)37:3<296::AID-ANIE296>3.0.CO
[4]  
2-U
[5]   The palladium-catalyzed C-H activation of benzylic gem-dialkyl groups [J].
Baudoin, O ;
Herrbach, A ;
Guéritte, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (46) :5736-5740
[6]   A concise stereoselective synthesis of Preussin, 3-epi-Preussin, and analogues [J].
Bertrand, Myra Beaudoin ;
Wolfe, John P. .
ORGANIC LETTERS, 2006, 8 (11) :2353-2356
[7]   REDUCTIVE COUPLING OF AROMATIC KETONES BY LOW-VALENT TITANIUM SALTS [J].
BOTTINO, FA ;
FINOCCHIARO, P ;
LIBERTINI, E ;
REALE, A ;
RECCA, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1982, (01) :77-81
[8]   A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction [J].
Bressy, C ;
Alberico, D ;
Lautens, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13148-13149
[9]   A tandem Heck-carbocyclization/Suzuki-coupling approach to the stereoselective syntheses of asymmetric 3,3-(diarylmethylene)indolinones [J].
Cheung, WS ;
Patch, RJ ;
Player, MR .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3741-3744
[10]   The virtue of palladium-catalyzed domino reactions -: Diverse oligocyclizations of acyclic 2-bromoenynes and 2-bromoenediynes [J].
De Meijere, A ;
Von Zezschwitz, P ;
Bräse, S .
ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (05) :413-422