Palladium-phosphinous acid-catalyzed Sonogashira cross-coupling reactions in water

被引:96
作者
Wolf, C [1 ]
Lerebours, R [1 ]
机构
[1] Georgetown Univ, Dept Chem, Washington, DC 20057 USA
关键词
D O I
10.1039/b407773c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-phosphinous acid-catalyzed Sonogashira cross-coupling reaction that proceeds in water under air atmosphere in the absence of organic co-solvents has been developed. Disubstituted alkynes have been prepared in up to 91% yield by POPd-catalyzed coupling of various aryl halides including chlorides in the presence of tetrabutylammonium bromide and pyrrolidine or NaOH.
引用
收藏
页码:2161 / 2164
页数:4
相关论文
共 85 条
[1]   Highly active oxime-derived palladacycle complexes for Suzuki-Miyaura and Ullmann-type coupling reactions [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5588-5594
[2]   NEW SYNTHETIC APPLICATIONS OF WATER-SOLUBLE ACETATE PD/TPPTS CATALYST GENERATED IN-SITU - EVIDENCE FOR A TRUE PD(0) SPECIES INTERMEDIATE [J].
AMATORE, C ;
BLART, E ;
GENET, JP ;
JUTAND, A ;
LEMAIREAUDOIRE, S ;
SAVIGNAC, M .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6829-6839
[3]   The Suzuki coupling of aryl chlorides in TBAB-water mixtures [J].
Bedford, RB ;
Blake, ME ;
Butts, CP ;
Holder, D .
CHEMICAL COMMUNICATIONS, 2003, (04) :466-467
[4]   Simple tricyclohexylphosphine-palladium complexes as efficient catalysts for the Stille coupling of deactivated aryl chlorides [J].
Bedford, RB ;
Cazin, CSJ ;
Hazelwood, SL .
CHEMICAL COMMUNICATIONS, 2002, (22) :2608-2609
[5]   Extremely high activity catalysts for the Suzuki coupling of aryl chlorides: the importance of catalyst longevity [J].
Bedford, RB ;
Hazelwood, SL ;
Limmert, ME .
CHEMICAL COMMUNICATIONS, 2002, (22) :2610-2611
[6]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[7]  
Böhm VPW, 2000, ANGEW CHEM INT EDIT, V39, P1602, DOI 10.1002/(SICI)1521-3773(20000502)39:9<1602::AID-ANIE1602>3.0.CO
[8]  
2-N
[9]  
Böhm VPW, 2000, CHEM-EUR J, V6, P1017, DOI 10.1002/(SICI)1521-3765(20000317)6:6<1017::AID-CHEM1017>3.0.CO
[10]  
2-8