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

Literature Information

Publication Date 2016-03-01
DOI 10.1039/C5QO00421G
Impact Factor 5.281
Authors

W. A. Nack, B. Wang, X. Wu, R. Jiao, G. He


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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.

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Organic Chemistry Frontiers

Organic Chemistry Frontiers
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Self-citation Rate: 8.7%
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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