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J Am Chem Soc. 2008 Nov 5;130(44):14422-3. doi: 10.1021/ja806244b. Epub 2008 Oct 8.

Cross-coupling reactions of aryl pivalates with boronic acids.

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  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA.

Abstract

The first cross-coupling of acylated phenol derivatives has been achieved. In the presence of an air-stable Ni(II) complex, readily accessible aryl pivalates participate in the Suzuki-Miyaura coupling with arylboronic acids. The process is tolerant of considerable variation in each of the cross-coupling components. In addition, a one-pot acylation/cross-coupling sequence has been developed. The potential to utilize an aryl pivalate as a directing group has also been demonstrated, along with the ability to sequentially cross-couple an aryl bromide followed by an aryl pivalate, using palladium and nickel catalysis, respectively.

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