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Ligand-Controlled Copper(I)-Catalyzed Cross-Coupling of Secondary and Primary Alcohols to α-Alkylated Ketones, Pyridines, and Quinolines

Da-Wei Tan, Hong-Xi Li*, Da-Liang Zhu, Hai-Yan Li, David James Young, Jian-Lin Yao* and Jian-Ping Lang*

*College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China, Email: lihxsuda.edu.cn, jlyaosuda.edu.cn, jplangsuda.edu.cn

D.-W. Tan, H.-X. Li, D.-L. Zhu, H.-Y. Li, D. J. Young, J.-L. Yao, J.-P. Lang, Org. Lett., 2018, 20, 608-611.

DOI: 10.1021/acs.orglett.7b03726 (free Supporting Information)



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Abstract

A hexanuclear Cu(I) cluster of 4,6-dimethylpyrimidine-2-thiolate efficiently catalyzes a dehydrogenative cross-coupling of primary and secondary alcohols to α-alkylated ketones. This transformation proceeds through a one-pot sequence of dehydrogenation of the alcohols, aldol condensation, hydrogenation, and dehydrogenation. This catalytic system also enables annulation reactions to yield pyridines and quinolines.

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proposed reaction pathway



Key Words

alkylation


ID: J54-Y2018