Nickel-Catalyzed Cross-Coupling Reaction of Alkenyl Methyl Ethers with Aryl Boronic Esters

被引:106
作者
Shimasaki, Toshiaki [1 ]
Konno, Yuko [2 ]
Tobisu, Mamoru [1 ]
Chatani, Naoto [2 ]
机构
[1] Osaka Univ, Grad Sch Engn, Frontier Res Base Global Young Res, Suita, Osaka 5650871, Japan
[2] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan
关键词
CARBON-OXYGEN BONDS; C-O ACTIVATION; ORGANOBORON COMPOUNDS; REAGENTS; BIARYLS; SALTS; ACIDS; FUNCTIONALIZATION; DERIVATIVES; CLEAVAGE;
D O I
10.1021/ol901978e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Ni(0)-catalyzed cross-coupling of alkenyl methyl ethers with boronic esters is described. Several types of alkenyl methyl ethers can be coupled with a wide range of boronic esters to give the stilbene derivatives.
引用
收藏
页码:4890 / 4892
页数:3
相关论文
共 31 条
[1]   The first Suzuki cross-couplings of aryltrimethylammonium salts [J].
Blakey, SB ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) :6046-6047
[2]   Nickel-catalyzed cross-coupling of aryl Grignard reagents with aromatic alkyl ethers: An efficient synthesis of unsymmetrical biaryls [J].
Dankwardt, JW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (18) :2428-2432
[3]  
de Meijere A., 2004, METAL CATALYZED CROS
[4]   Palladium-catalyzed Suzuki-Miyaura cross-couplings of sulfonyl chlorides and boronic acids [J].
Dubbaka, SR ;
Vogel, P .
ORGANIC LETTERS, 2004, 6 (01) :95-98
[5]   New synthesis of biaryls via Rh-catalyzed decarbonylative Suzuki-coupling of carboxylic anhydrides with arylboroxines [J].
Goossen, LJ ;
Paetzold, J .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1665-1668
[6]   Biaryl Construction via Ni-Catalyzed C-O Activation of Phenolic Carboxylates [J].
Guan, Bing-Tao ;
Wang, Yang ;
Li, Bi-Jie ;
Yu, Da-Gang ;
Shi, Zhang-Jie .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) :14468-+
[7]   Methylation of arenes via Ni-catalyzed aryl C-O/F activation [J].
Guan, Bing-Tao ;
Xiang, Shi-Kai ;
Wu, Tao ;
Sun, Zuo-Peng ;
Wang, Bi-Qin ;
Zhao, Ke-Qing ;
Shi, Zhang-Jie .
CHEMICAL COMMUNICATIONS, 2008, (12) :1437-1439
[8]   Direct benzylic alkylation via Ni-catalyzed selective benzylic sp3 C-O activation [J].
Guan, Bing-Tao ;
Xiang, Shi-Kai ;
Wang, Bi-Qin ;
Sun, Zuo-Peng ;
Wang, Yang ;
Zhao, Ke-Qing ;
Shi, Zhang-Jie .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3268-+
[9]   Tetraarylphosphonium halides as arylating reagents in Pd-catalyzed Heck and cross-coupling reactions [J].
Hwang, LK ;
Na, Y ;
Lee, J ;
Do, Y ;
Chang, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6166-6169
[10]   Ruthenium-catalyzed functionalization of aryl carbon-oxygen bonds in aromatic ethers with organoboron compounds [J].
Kakiuchi, F ;
Usui, M ;
Ueno, S ;
Chatani, N ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (09) :2706-2707