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; Jian-Ping Lang

doi:10.1021/acs.orglett.7b03726

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

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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

Organic Letters, Vol.20(3), pp.608-611

2018

DOI: https://doi.org/10.1021/acs.orglett.7b03726

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Abstract

One hexanuclear Cu(I) cluster of 4,6-dimethylpyrimidine-2-thiolate efficiently catalyzes the dehydrogenative cross-coupling of secondary and primary alcohols to α-alkylated ketones with high selectivity. This transformation proceeds through a one-pot sequence of dehydrogenation of alcohols, condensation of aldehydes and ketones, hydrogenation of the resulting α,β-unsaturated ketones, and dehydrogenation of the α-alkylated alcohols to generate α-alkylated ketones. This catalytic system also displays high activity for the annulation reaction of secondary alcohols with γ-amino- and 2-aminobenzyl alcohols to yield pyridines and quinolines, respectively.

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Title: Ligand-Controlled Copper(I)-Catalyzed Cross-Coupling of Secondary and Primary Alcohols to α-Alkylated Ketones, Pyridines, and Quinolines
Authors: Da-Wei Tan (Author) - Soochow University, China
Hong-Xi Li (Author) - Soochow University, China
Da-Liang Zhu (Author) - Soochow University, China
Hai-Yan Li (Author) - Soochow University, China
David James Young (Author) - University of the Sunshine Coast - Faculty of Science, Health, Education and Engineering
Jian-Lin Yao (Author) - Soochow University, China
Jian-Ping Lang (Author) - Soochow University, China
Publication details: Organic Letters, Vol.20(3), pp.608-611
Publisher: American Chemical Society
Date published: 2018
DOI: 10.1021/acs.orglett.7b03726
ISSN: 1523-7060; 1523-7060
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99451415902621
Output Type: Journal article

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Collaboration types: Domestic collaboration; International collaboration
Web Of Science research areas: Chemistry, Organic