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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 17
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Original Articles

Betti Base as an Efficient Ligand for Copper-Catalyzed Ullmann Coupling of Phenol with Aryl Halides

, , , &
Pages 2468-2477 | Received 04 Dec 2013, Published online: 01 Jul 2014
 

Abstract

A simple, general, and highly efficient Betti base ligand has been developed for copper-catalyzed Ullmann coupling of phenol with aryl halides without the protection of an inert atmosphere. The reaction proceeds smoothly in the presence of K2CO3 as the base and dimethylsulfoxide as the solvent. The catalyst was reused several times with no evident loss of catalytic activity and is environmentally friendly.

GRAPHICAL ABSTRACT

Notes

a Reaction conditions: iodobenzene (1.0 mmol), m-cresol (1.0 mmol), CuX (0.1 mmol), L (0.2 mmol), 2.0 equiv base, solvent (3 mL), 120 °C.

b GC yield determined by using methoxybenzene as internal standard.

c Reaction temperature is 80 °C.

d Without L.

a Reaction conditions: iodobenzene (1.0 mmol), phenol (1.0 mmol), CuI (0.1 mmol), L1 (0.2 mmol), 2.0 equiv K2CO3, DMSO (3 mL), 120 °C. b Isolated yield.

a Reaction conditions: aryl halides (1.0 mmol), m-cresol (1.0 mmol), CuI (0.1 mmol), L1 (0.2 mmol), 2.0 equiv K2CO3, DMSO (3 mL), 120 °C.

b Isolated yield.

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