Palladium-phosphinous acid-catalyzed NaOH-promoted cross-coupling reactions of arylsiloxanes with aryl chlorides and bromides in water

被引：143

作者：

Wolf, C ^{[1
]}

Lerebours, R ^{[1
]}

机构：

[1] Georgetown Univ, Dept Chem, Washington, DC 20057 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 07期

关键词：

D O I：

10.1021/ol049851s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-phosphinous acid-catalyzed and NaOH-promoted coupling method using arylsiloxanes and aryl halides in water has been developed. The POPd1-catalyzed reaction between aryl chlorides or bromides and arylsiloxanes is compatible with various functional groups and affords biaryls in up to 99% yield. This cross-coupling reaction does not require additives such as surfactants or organic cosolvents and proceeds under air, which greatly facilitates operation and catalyst handling.

引用

页码：1147 / 1150

页数：4

共 68 条

[1] Highly active oxime-derived palladacycle complexes for Suzuki-Miyaura and Ullmann-type coupling reactions
Alonso, DA
Nájera, C
Pacheco, MC
[J]. 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
AMATORE, C
BLART, E
GENET, JP
JUTAND, A
LEMAIREAUDOIRE, S
SAVIGNAC, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) : 6829 - 6839
[3] Highly efficient palladium-catalyzed boronic acid coupling reactions in water: Scope and limitations
Badone, D
Baroni, M
Cardamone, R
Ielmini, A
Guzzi, U
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) : 7170 - 7173
[4] BEDRORD RB, 2003, CHEM COMMUN, P466
[5] Cross-coupling reactions with boronic acids in water catalysed by oxime-derived palladacycles
Botella, L
Nájera, C
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 663 (1-2) : 46 - 57
[6] Botella L, 2002, ANGEW CHEM INT EDIT, V41, P179, DOI 10.1002/1521-3773(20020104)41:1<179::AID-ANIE179>3.0.CO
[7] 2-O
[8] Stereoselective phenylation of allylic alcohol derivatives by palladium-catalyzed cross-coupling with hypervalent silicon complexes
Brescia, MR
DeShong, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) : 3156 - 3157
[9] REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES
CHUIT, C
CORRIU, RJP
REYE, C
YOUNG, JC
[J]. CHEMICAL REVIEWS, 1993, 93 (04) : 1371 - 1448
[10] Palladium-catalyzed arylation of allylic benzoates using hypervalent siloxane derivatives
Correia, R
DeShong, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21) : 7159 - 7165

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