Suzuki coupling of aryl chlorides with phenylboronic acid in water, using microwave heating with simultaneous cooling

被引：245

作者：

Arvela, RK ^{[1
]}

Leadbeater, NE ^{[1
]}

机构：

[1] Univ Connecticut, Dept Chem, Unit 3060, Storrs, CT 06269 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 11期

关键词：

D O I：

10.1021/ol0503384

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We present here a methodology for the Suzuki coupling of aryl chlorides with phenylboronic acid using Pd/C as a catalyst, water as a solvent, and microwave heating. We show that simultaneous cooling in conjunction with microwave heating prolongs the lifetime of the aryl chloride substrates during the course of the reaction and, as a result, yields of the desired biaryl as well as overall recovery of material can be increased.

引用

页码：2101 / 2104

页数：4

共 55 条

[1] Synthetic applications of oxime-derived palladacycles as versatile catalysts in cross-coupling reactions
Alonso, DA
Botella, L
Nájera, C
Pacheco, C
[J]. SYNTHESIS-STUTTGART, 2004, (10): : 1713 - 1718
[2] A reassessment of the transition-metal free Suzuki-type coupling methodology
Arvela, RK
Leadbeater, NE
Sangi, MS
Williams, VA
Granados, P
Singer, RD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) : 161 - 168
[3] The development of palladium catalysts for C-C and C-heteroatom bond forming reactions of aryl chloride substrates
Bedford, RB
Cazin, CSJ
Holder, D
[J]. COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) : 2283 - 2321
[4] Palladacyclic catalysts in C-C and C-heteroatom bond-forming reactions
Bedford, RB
[J]. CHEMICAL COMMUNICATIONS, 2003, (15) : 1787 - 1796
[5] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances
Bellina, F
Carpita, A
Rossi, R
[J]. SYNTHESIS-STUTTGART, 2004, (15): : 2419 - 2440
[6] 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
[7] MICROWAVE-ASSISTED ORGANIC-REACTIONS
CADDICK, S
[J]. TETRAHEDRON, 1995, 51 (38) : 10403 - 10432
[8] An efficient catalyst for Suzuki-Miyaura coupling reaction in aqueous medium under aerobic conditions
Chen, CL
Liu, YH
Peng, SM
Liu, ST
[J]. TETRAHEDRON LETTERS, 2005, 46 (03) : 521 - 523
[9] Rapid synthesis of α-ketoamides using microwave irradiation-simultaneous cooling method
Chen, JJ
Deshpande, SV
[J]. TETRAHEDRON LETTERS, 2003, 44 (49) : 8873 - 8876
[10] Metalated heterocycles and their applications in synthetic organic chemistry
Chinchilla, R
Nájera, C
Yus, M
[J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2667 - 2722

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