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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 7
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Original Articles

Remarkably Facile Heck Reactions in Aqueous Two-Phase System Catalyzed by Reusable Pd/C Under Ligand-Free Conditions

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Pages 1059-1069 | Received 01 Jun 2010, Published online: 16 Dec 2011
 

Abstract

A fast and convenient Heck reaction was achieved catalyzed by Pd/C in aqueous two-phase system. The aqueous two-phase system has been shown to be a highly active solvent for Heck reactions of aryl halides even in the absence of organic ligands.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

This work was supported by the Natural Science Foundation of Zhejiang Province, China (Project Y407240), and the Key Science Foundation of Lishui University (Project KY07002).

Notes

a Reaction condition: 3 mmol PhI, 3.3 mmol methyl acrylate, 3 mol% Pd/C, 8 mmol base (or phase separation salts), and solvent (10 mL), reflux at 80 °C for corresponding time by GC or TLC.

b Isolated yield.

c Added CTAB.

a Reaction condition: 3 mmol PhI, 3.3 mmol methyl acrylate, 8 mmol base, 3 mol% Pd/C, ethanol 6 ml, and water 4 ml, reflux at 80 °C for corresponding time by GC.

b Isolated yield.

a Reaction condition: 3 mmol ArX, 3.3 mmol olefin, 8 mmol K2HPO4, and 3 mol % Pd/C, aqueous two-phase system (10 mL) reflux at 80 °C for corresponding time by GC or TLC.

b MA: CH2 = CHCO2CH3, BA: CH2 = CHCO2(Bu-n), PTEA: CH2 = CHCO2CH2CH2SPh.

c Isolated yield.

d Exit about 1.4–2.0% double-substituted product from the GC/MS.

a In entry 2, 1.5 mol% Pd/C was used.

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