Issue 5, 2016

Palladium-catalyzed arylation of β-methylene C(sp3)–H bonds at room temperature: desymmetrization of simple cycloalkyl carboxylic acids

Abstract

A new protocol for Pd-catalyzed β methylene C–H arylation of N-quinolyl cycloalkylcarboxamides with aryl iodides at room temperature is reported. The β methylene C–H bonds of symmetrical cycloalkylcarboxamides of varied ring size can be arylated in moderate to good yields and monoselectivity with excellent diastereoselectivity. This mono-selective β methylene C–H arylation reaction enabled the rapid synthesis of complex carbocycle products from easily accessible symmetrical cycloalkyl carboxylic acids via sequential C–H functionalization.

Graphical abstract: Palladium-catalyzed arylation of β-methylene C(sp3)–H bonds at room temperature: desymmetrization of simple cycloalkyl carboxylic acids

Supplementary files

Article information

Article type
Research Article
Submitted
11 Kax 2015
Accepted
17 Nah 2016
First published
01 Cig 2016

Org. Chem. Front., 2016,3, 561-564

Palladium-catalyzed arylation of β-methylene C(sp3)–H bonds at room temperature: desymmetrization of simple cycloalkyl carboxylic acids

W. A. Nack, B. Wang, X. Wu, R. Jiao, G. He and G. Chen, Org. Chem. Front., 2016, 3, 561 DOI: 10.1039/C5QO00421G

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