Palladium-catalyzed Sonogashira and Hiyama reactions using phosphine-free hydrazone Ligands

被引:91
作者
Mino, Takashi [1 ]
Shirae, Yoshiaki [1 ]
Saito, Takeshi [1 ]
Sakamoto, Masami [1 ]
Fujita, Tsutomu [1 ]
机构
[1] Chiba Univ, Dept Appl Chem & Biotechnol, Fac Engn, Inage Ku, Chiba 2638522, Japan
关键词
D O I
10.1021/jo061734i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium/copper-catalyzed Sonogashira cross-coupling reaction of aryl halides with a variety of terminal alkynes under amine-free conditions in dimethylformamide (DMF) at 80 degrees C gave internal arylated alkynes using PdCl2(MeCN)(2) with phosphine-free hydrazone 2a as a ligand and CuI as the cocatalyst in good yields. We also found PdCl2/hydrazone ligand 1d in PhMe at 80 degrees C was a phosphine-free efficient catalyst system for a Hiyama cross-coupling reaction of aryl bromides with aryl(trialkoxy)silanes in good yields.
引用
收藏
页码:9499 / 9502
页数:4
相关论文
共 51 条
[1]   Palladium complexes of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane:: Synthesis, crystal structure and use in the Suzuki and Sonogashira reactions and the α-arylation of ketones [J].
Adjabeng, G ;
Brenstrum, T ;
Frampton, CS ;
Robertson, AJ ;
Hillhouse, J ;
McNulty, J ;
Capretta, A .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :5082-5086
[2]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[3]  
BELLER M, 1998, TRANSITION METALS OR, V1, P208
[4]  
Brase S, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P99
[5]   Stereoselective phenylation of allylic alcohol derivatives by palladium-catalyzed cross-coupling with hypervalent silicon complexes [J].
Brescia, MR ;
DeShong, P .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3156-3157
[6]  
BRNDSMA L, 1998, APPL TRANSITION META, pCH10
[7]   SYNTHESIS OF ARYL-SUBSTITUTED AND VINYL-SUBSTITUTED ACETYLENE DERIVATIVES BY USE OF NICKEL AND PALLADIUM COMPLEXES [J].
CASSAR, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :253-257
[8]   A copper- and amine-free sonogashira reaction employing aminophosphines as ligands [J].
Cheng, J ;
Sun, YH ;
Wang, F ;
Guo, MJ ;
Xu, JH ;
Pan, Y ;
Zhang, ZG .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5428-5432
[9]   A highly selective synthesis of diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction under phase transfer conditions [J].
Chow, HF ;
Wan, CW ;
Low, KH ;
Yeung, YY .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1910-1913
[10]  
Crisp GT, 1998, CHEM SOC REV, V27, P427