Sonogashira coupling of aryl halides catalyzed by palladium on charcoal

被引：182

作者：

Novák, Z

Szabó, A

Répási, J

Kotschy, A

机构：

[1] Eotvos Lorand Univ, Dept Gen & Inorgan Chem, H-1117 Budapest, Hungary

[2] Ubichem Res Plc, H-1025 Budapest, Hungary

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 08期

关键词：

D O I：

10.1021/jo034149f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

With the proper choice of solvent, palladium on charcoal acts as an efficient catalyst in the Sonogashira cross-coupling reaction of aryl bromides. The catalytically active species in the process is probably palladium, which leaches into the solution but returns onto the surface of the charcoal at the end of the reaction.

引用

页码：3327 / 3329

页数：3

共 30 条

[1] HETEROGENEOUS CATALYSIS IN ORGANIC-CHEMISTRY .10. EFFECT OF THE CATALYST SUPPORT ON THE REGIOCHEMISTRY OF THE HECK ARYLATION REACTION
AUGUSTINE, RL
OLEARY, ST
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 95 (03) : 277 - 285
[2] The pyridinium reduction route to alkaloids:: a synthesis of (±)-tashiromine
Bates, RW
Boonsombat, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (07): : 654 - 656
[3] BLEICHER L, 1995, SYNLETT, P1115
[4] A practical and efficient synthesis of the selective neuronal acetylcholine-gated ion channel agonist (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine maleate (SIB-1508Y)
Bleicher, LS
Cosford, NDP
Herbaut, A
McCallum, JS
McDonald, IA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) : 1109 - 1118
[5] Catalytic coupling of terminal acetylenes with iodoarenes and diaryliodonium salts in water
Bumagin, NA
Sukhomlinova, LI
Luzikova, EV
Tolstaya, TP
Beletskaya, IP
[J]. TETRAHEDRON LETTERS, 1996, 37 (06) : 897 - 900
[6] (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y): A novel anti-Parkinsonian agent with selectivity for neuronal nicotinic acetylcholine receptors
Cosford, NDP
Bleicher, L
Herbaut, A
McCallum, JS
Vernier, JM
Dawson, H
Whitten, JP
Adams, P
ChavezNoriega, L
Correa, LD
Crona, JH
Mahaffy, LS
Menzaghi, F
Rao, TS
Reid, R
Sacaan, AI
Santori, E
Stauderman, KA
Whelan, K
Lloyd, GK
McDonald, IA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (17) : 3235 - 3237
[7] CROSS-COUPLING REACTIONS OF MONOSUBSTITUTED ACETYLENES AND ARYL HALIDES CATALYZED BY PALLADIUM ON CHARCOAL
DELAROSA, MA
VELARDE, E
GUZMAN, A
[J]. SYNTHETIC COMMUNICATIONS, 1990, 20 (13) : 2059 - 2064
[8] Heck reaction catalyzed by Pd-modified zeolites
Djakovitch, L
Koehler, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (25) : 5990 - 5999
[9] Multikilogram-scale synthesis at a biphenyl carboxylic acid derivative using a Pd/C-mediated Suzuki coupling approach
Ennis, DS
McManus, J
Wood-Kaczmar, W
Richardson, J
Smith, GE
Carstairs, A
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1999, 3 (04) : 248 - 252
[10] Rapid homogeneous-phase Sonogashira coupling reactions using controlled microwave heating
Erdélyi, M
Gogoll, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) : 4165 - 4169

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