Organic Chemistry Portal



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:,,

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

see article for more reactions


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.

see article for more examples

proposed reaction pathway

Key Words


ID: J54-Y2018