Ligand-Free Palladium-Catalyzed Direct Arylation of Thiazoles at Low Catalyst Loadings

被引：113

作者：

Roger, Julien ^{[1
]}

Pozgan, Franc ^{[1
]}

Doucet, Henri ^{[1
]}

机构：

[1] Univ Rennes Catalyse & Organomet, CNRS, UMR 6226, Inst Sci Chim Rennes, F-35042 Rennes, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 03期

关键词：

USEFUL COUPLING PARTNERS; C-H FUNCTIONALIZATION; ARYL CHLORIDES; HECK REACTIONS; BOND FORMATION; PLASMEPSIN-I; HETEROAROMATICS; ACTIVATION; HALIDES; ACCESS;

D O I：

10.1021/jo802360d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ligand-free Pd(OAc)(2) was found to catalyze very efficiently the direct arylation of thiazole derivatives under very low catalyst concentration. By using activated aryl bromides, the reaction can be performed employing as little as 0.1-0.001 mol % catalyst. With such substrates, this procedure is economically and environmentally attractive. On the other hand, in the presence of more challenging substrates, such as some strongly deactivated or highly congested aryl bromides, in some cases, disappointing results were obtained.

引用

页码：1179 / 1186

页数：8

共 43 条

[21] Comparing the Reactivity of the 4- and 5-positions of 2-phenylthiazoles in Stille cross-coupling reactions
Haemmerle, Johanna
Schnuerch, Michael
Stanetty, Peter
[J]. SYNLETT, 2007, (19) : 2975 - 2978
[22] Hara O, 2006, HETEROCYCLES, V68, P1
[23] Jensen J, 2001, SYNTHESIS-STUTTGART, P128
[24] Introduction of ethynylene and thienylene spacers into 2,5-diarylthiazole and 2,5-diarylthiophene
Kobayashi, Kei
Ahmed, Mohamed S. Mohamed
Mori, Atsunori
[J]. TETRAHEDRON, 2006, 62 (41) : 9548 - 9553
[25] Li J.J., 2000, PALLADIUM HETEROCYCL
[26] Direct C-2 arylation of alkyl 4-thiazolecarboxylates: New insights in synthesis of heterocyclic core of thiopeptide antibiotics
Martin, Thibaut
Verrier, Cecile
Hoarau, Christophe
Marsais, Francis
[J]. ORGANIC LETTERS, 2008, 10 (13) : 2909 - 2912
[27] Syntheses and properties of donor-acceptor-type 2,5-diarylthiophene and 2,5-diarylthiazole
Masui, K
Mori, A
Okano, K
Takamura, K
Kinoshita, M
Ikeda, T
[J]. ORGANIC LETTERS, 2004, 6 (12) : 2011 - 2014
[28] Facile synthesis of 2,5-diarylthiazoles via palladium-catalyzed tandem C-H substitutions. Design of tunable light emission and liquid crystalline characteristics
Mori, A
Sekiguchi, A
Masui, K
Shimada, T
Horie, M
Osakada, K
Kawamoto, M
Ikeda, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) : 1700 - 1701
[29] PALLADIUM-CATALYZED ARYLATION OF FURAN, THIOPHENE, BENZO[B]FURAN AND BENZO[B]THIOPHENE
OHTA, A
AKITA, Y
OHKUWA, T
CHIBA, M
FUKUNAGA, R
MIYAFUJI, A
NAKATA, T
TANI, N
AOYAGI, Y
[J]. HETEROCYCLES, 1990, 31 (11) : 1951 - 1958
[30] New potent C2-symmetric malaria plasmepsin I and II inhibitors
Oscarsson, K
Oscarson, S
Vrang, L
Hamelink, E
Hallberg, A
Samuelsson, B
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (07) : 1235 - 1246

← 1 2 3 4 5 →