A general and efficient catalyst for palladium-catalyzed C-O coupling reactions of aryl halides with primary alcohols.

Saravanan Gowrisankar, Alexey G Sergeev, Pazhamalai Anbarasan, Anke Spannenberg, Helfried Neumann, Matthias Beller

Index: J. Am. Chem. Soc. 132 , 11592, (2010)

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Abstract

An efficient procedure for palladium-catalyzed coupling reactions of (hetero)aryl bromides and chlorides with primary aliphatic alcohols has been developed. Key to the success is the synthesis and exploitation of the novel bulky di-1-adamantyl-substituted bipyrazolylphosphine ligand L6. Reaction of aryl halides including activated, nonactivated, and (hetero)aryl bromides as well as aryl chlorides with primary alcohols gave the corresponding alkyl aryl ethers in high yield. Noteworthy, functionalizations of primary alcohols in the presence of secondary and tertiary alcohols proceed with excellent regioselectivity.