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Overcoming the Naphthyl Requirement in Stereospecific Cross-Couplings to Form Quaternary Stereocenters

Jianyu Xu, Olivia P. Bercher and Mary P. Watson*

*Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States, Email:

J. Xu, O. P. Bercher, M. P. Watson, J. Am. Chem. Soc., 2021, 143, 8608-8613.

DOI: 10.1021/jacs.1c03898

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The use of a simple stilbene ligand enables a stereospecific Suzuki-Miyaura cross-coupling of chiral tertiary benzylic carboxylates to provide challenging all-carbon diaryl quaternary stereocenters in good yield and ee. Precedent reaction systems required substrates substituted with naphthyl groups or specific heteroaryls to obtain high yields and stereochemical fidelities.

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Key Words

Suzuki coupling, diarylmethanes

ID: J48-Y2021