Base and cation effects on the Suzuki cross-coupling of bulky arylboronic acid with halopyridines: Synthesis of pyridylphenols

被引:86
作者
Zhang, HC [1 ]
Kwong, FY [1 ]
Tian, Y [1 ]
Chan, KS [1 ]
机构
[1] Chinese Univ Hong Kong, Dept Chem, Shatin, NT, Peoples R China
关键词
D O I
10.1021/jo980646y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Strong base and large size cation have been shown to accelerate the rate and the yield of Suzuki coupling of a sterically bulky boronic acid with halopyridines in DME for the synthesis of pyridylphenols.
引用
收藏
页码:6886 / 6890
页数:5
相关论文
共 43 条
[1]   SYNTHESIS AND RESOLUTION OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE - A P-N CHELATING LIGAND FOR ASYMMETRIC CATALYSIS [J].
ALCOCK, NW ;
BROWN, JM ;
HULMES, DI .
TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :743-756
[2]   OBSERVATION OF CATALYTIC INTERMEDIATES IN THE SUZUKI REACTION BY ELECTROSPRAY MASS-SPECTROMETRY [J].
ALIPRANTIS, AO ;
CANARY, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6985-6986
[3]  
ANDERSON JC, 1995, SYNLETT, P765
[4]   HIGH YIELDS OF UNSYMMETRICAL BIARYLS VIA CROSS-COUPLING OF ARYLBORONIC ACIDS WITH HALOARENES USING A MODIFIED SUZUKI-BELETSKAYA PROCEDURE [J].
CAMPI, EM ;
JACKSON, WR ;
MARCUCCIO, SM ;
NAESLUND, CGM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (20) :2395-2395
[5]   THE SYNTHESIS OF CERTAIN SUBSTITUTED 2,2'-BIPYRIDYLS [J].
CASE, FH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, 68 (12) :2574-2577
[6]   SYNTHESIS OF BETA-ARYL SUBSTITUTED PORPHYRINS BY PALLADIUM-CATALYZED SUZUKI CROSS-COUPLING REACTIONS [J].
CHAN, KS ;
ZHOU, XA ;
AU, MT ;
TAM, CY .
TETRAHEDRON, 1995, 51 (11) :3129-3136
[7]   Synthesis of contiguous cyclopropanes by palladium-catalyzed Suzuki-type cross-coupling reactions. [J].
Charette, AB ;
DeFreitasGil, RP .
TETRAHEDRON LETTERS, 1997, 38 (16) :2809-2812
[8]  
Cotton F.A., 1988, Advanced Inorganic Chemistry
[9]  
COZORT JR, 1983, J ORG CHEM, V48, P4190, DOI 10.1021/jo00171a007
[10]   TEMPLATED SYNTHESIS OF INTERLOCKED MACROCYCLIC LIGANDS, THE CATENANDS - PREPARATION AND CHARACTERIZATION OF THE PROTOTYPICAL BIS-30 MEMBERED RING-SYSTEM [J].
DIETRICHBUCHECKER, C ;
SAUVAGE, JP .
TETRAHEDRON, 1990, 46 (02) :503-512