Nickel-catalyzed addition of organoboronates to 1,2-dienes and the corresponding three-component reaction with an alkyne

被引:26
作者
Takahashi, Go
Shirakawa, Eiji [1 ]
Tsuchimoto, Teruhisa
Kawakami, Yusuke
机构
[1] Japan Adv Inst Sci & Technol, Grad Sch Mat Sci, Nomi, Ishikawa 9231292, Japan
[2] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
关键词
alkynes; allenes; arylboronates; hydroalkenylation; hydroarylation; nickel;
D O I
10.1002/adsc.200505445
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A Ni(cod)(2)-aminophosphine complex catalyzed the addition of aryl- and alkenylboronates to 1,2-dienes to give the hydroarylation and hydroalkenylation products of the 1,2-dienes, whereas the hydroarylation products of a 1,2-diene and an alkyne were obtained with a Ni(cod)(2)-PPh3 catalyst.
引用
收藏
页码:837 / 840
页数:4
相关论文
共 18 条
[1]   Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].
Fagnou, K ;
Lautens, M .
CHEMICAL REVIEWS, 2003, 103 (01) :169-196
[2]   Unprecedented carbocyclization of 1,6-allenynes on addition of organoboronic acids under Pd-catalysis [J].
Gupta, AK ;
Rhim, CY ;
Oh, CH .
TETRAHEDRON LETTERS, 2005, 46 (13) :2247-2250
[3]   Rhodium-catalyzed hydroarylation of alkynes with arylboronic acids: 1,4-shift of rhodium from 2-aryl-1-alkenylrhodium to 2-alkenylarylrhodium intermediate [J].
Hayashi, T ;
Inoue, K ;
Taniguchi, N ;
Ogasawara, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (40) :9918-9919
[4]   Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].
Hayashi, T ;
Yamasaki, K .
CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844
[5]   On the regioselectivity of Pd-catalyzed additions of organoboronic acids to unsymmetrical alkynes [J].
Kim, N ;
Kim, KS ;
Gupta, AK ;
Oh, CH .
CHEMICAL COMMUNICATIONS, 2004, (05) :618-619
[6]  
Krause N., 2004, MODERN ALLENE CHEM
[7]   Rhodium-catalyzed coupling reactions of arylboronic acids to olefins in aqueous media [J].
Lautens, M ;
Roy, A ;
Fukuoka, K ;
Fagnou, K ;
Martín-Matute, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) :5358-5359
[8]   Palladium-catalyzed highly regio- and stereoselective addition of organoboronic acids to allenes in the presence of AcOH [J].
Ma, SM ;
Jiao, N ;
Ye, LW .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (24) :6049-6056
[9]   Merry-go-round multiple alkylation on aromatic rings via rhodium catalysis [J].
Oguma, K ;
Miura, M ;
Satoh, T ;
Nomura, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (42) :10464-10465
[10]   Palladium-catalyzed addition of organoboronic acids to allenes [J].
Oh, CH ;
Ahn, TW ;
Reddy, RV .
CHEMICAL COMMUNICATIONS, 2003, (20) :2622-2623