Issue 16, 2014

Copper-catalyzed benzylic C(sp3)–H alkoxylation of heterocyclic compounds

Abstract

We achieved intra- and intermolecular C(sp3)–H alkoxylation of benzylic positions of heteroaromatic compounds using CuBrn (n = 1, 2)/5,6-dimethylphenanthroline (or 4,7-dimethoxyphenanthroline) and (tBuO)2 as a catalyst and an oxidant, respectively. The reaction proceeded at both terminal and internal benzylic positions of the alkyl groups. The intramolecular alkoxylation was performed on a gram scale.

Graphical abstract: Copper-catalyzed benzylic C(sp3)–H alkoxylation of heterocyclic compounds

Supplementary files

Article information

Article type
Communication
Submitted
27 Jan 2014
Accepted
20 Feb 2014
First published
21 Feb 2014

Org. Biomol. Chem., 2014,12, 2528-2532

Author version available

Copper-catalyzed benzylic C(sp3)–H alkoxylation of heterocyclic compounds

N. Takemura, Y. Kuninobu and M. Kanai, Org. Biomol. Chem., 2014, 12, 2528 DOI: 10.1039/C4OB00215F

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