Issue 15, 2012
From the journal:

Organic & Biomolecular Chemistry

Copper-catalyzed C-alkylation of secondary alcohols and methyl ketones with alcohols employing the aerobic relay race methodology†

Shiheng Liao,a   Kangkang Yu,a   Qiang Li,a   Haiwen Tian,a   Zhengping Zhang,a   Xiaochun Yua  and  Qing Xu*a  

* Corresponding authors

a College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, China
E-mail: qing-xu@wzu.edu.cn
Fax: (+)-86-577-88373111
Tel: (+)-86-13857745327

Abstract

By employing aerobic oxidation to aldehydes as a more effective alcohol activation strategy, ligand-free copper catalysts were found to be superior catalysts than other metals in aerobic dehydrative β-alkylation of secondary alcohols and α-alkylation of methyl ketones using alcohols as the green alkylating reagents. Based on our mechanistic studies and also supported by the literature, we deduce that the newly-proposed relay race process rather than the conventional borrowing hydrogen-type mechanisms should be the most possible and a more rational mechanism for the aerobic C-alkylation reactions.

Graphical abstract: Copper-catalyzed C-alkylation of secondary alcohols and methyl ketones with alcohols employing the aerobic relay race methodology

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Article information

DOI
https://doi.org/10.1039/C1OB06739G
Article type
Paper
Submitted
14 Oct 2011
Accepted
21 Nov 2011
First published
20 Jan 2012

Org. Biomol. Chem., 2012,10, 2973-2978

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Copper-catalyzed C-alkylation of secondary alcohols and methyl ketones with alcohols employing the aerobic relay race methodology

S. Liao, K. Yu, Q. Li, H. Tian, Z. Zhang, X. Yu and Q. Xu, Org. Biomol. Chem., 2012, 10, 2973 DOI: 10.1039/C1OB06739G

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