Open-vessel microwave-promoted Suzuki reactions using low levels of palladium catalyst: Optimization and scale-up

被引：61

作者：

Leadbeater, Nicholas E.

Williams, Victoria A.

Barnard, Thomas M.

Collins, Michael J., Jr.

机构：

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

[2] CEM Microwave Technol, Matthews, NC 28104 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2006年 / 10卷 / 04期

关键词：

D O I：

10.1021/op0600613

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Representative Suzuki couplings in water using low catalyst concentrations in conjunction with microwave heating have been transferred from sealed-vessel to open-vessel reaction conditions. They have then been scaled-up to the mole scale using a dedicated multimode microwave apparatus. The reactions are complete within 20 min of heating at reflux.

引用

收藏

页码：833 / 837

页数：5

相关论文

共 57 条

[1] Reproducibility across microwave instruments:: First example of genuine parallel scale up of compounds under microwave irradiation [J].

Alcázar, J ;

Diels, G ;

Schoentjes, B .

QSAR & COMBINATORIAL SCIENCE, 2004, 23 (10) :906-910

[2]

[Anonymous], 2002, MICROWAVES ORGANIC S

[3] Suzuki coupling of aryl chlorides with phenylboronic acid in water, using microwave heating with simultaneous cooling [J].

Arvela, RK ;

Leadbeater, NE .

ORGANIC LETTERS, 2005, 7 (11) :2101-2104

[4] Microwave-promoted Suzuki coupling reactions with organotrifluoroborates in water using ultra-low catalyst loadings [J].

Arvela, RK ;

Leadbeater, NE ;

Mack, TL ;

Kormos, CM .

TETRAHEDRON LETTERS, 2006, 47 (02) :217-220

[5] Automated batch scale-up of microwave-promoted Suzuki and Heck coupling reactions in water using ultra-low metal catalyst concentrations [J].

Arvela, RK ;

Leadbeater, NE ;

Collins, MJ .

TETRAHEDRON, 2005, 61 (39) :9349-9355

[6] A reassessment of the transition-metal free Suzuki-type coupling methodology [J].

Arvela, RK ;

Leadbeater, NE ;

Sangi, MS ;

Williams, VA ;

Granados, P ;

Singer, RD .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :161-168

[7] A simple continuous flow microwave reactor [J].

Bagley, MC ;

Jenkins, RL ;

Lubinu, MC ;

Mason, C ;

Wood, R .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) :7003-7006

[8] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].

Bellina, F ;

Carpita, A ;

Rossi, R .

SYNTHESIS-STUTTGART, 2004, (15) :2419-2440

[9] DEVELOPMENT AND APPLICATION OF A CONTINUOUS MICROWAVE REACTOR FOR ORGANIC-SYNTHESIS [J].

CABLEWSKI, T ;

FAUX, AF ;

STRAUSS, CR .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3408-3412

[10] An efficient and cost-effective synthesis of 2-phenyl-3-aminopyridine [J].

Caron, S ;

Massett, SS ;

Bogle, DE ;

Castaldi, MJ ;

Braish, TF .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (03) :254-256

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