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β-Arylation of Carboxamides Via Iron-Catalyzed C(sp3)–H Bond Activation

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New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation

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Abstract

Directed C(sp3)–H bond functionalization has been studied mainly by using precious metal catalysts, such as Pd, Ru, Rh, and Ir under harsh conditions. Generally, these metal-catalyzed C–H functionalization reactions are based on the formation of a C(sp3)-metallacycle. Iron-catalyzed C(sp3)–H functionalization has been studied mainly using radical processes. Functionalization of an unactivated C(sp3)–H bond via formation of a ferracycle intermediate is limited to stoichiometric reactions. We report here an iron/biphosphine-catalyzed directed arylation of a C(sp3)–H bond in an aliphatic carboxamide with an organozinc reagent in high yield under mild oxidative conditions. The choice of the directing group and of the biphosphine ligand was crucial for the success of this reaction. This reaction shows selectivity for a primary C–H over a secondary one and is sensitive to steric factors on both the amide and the Grignard reagent. Various β-arylated aliphatic carboxamides can be readily prepared by using this method.

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  1. Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, China

    Rui Shang

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  1. Rui Shang
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Correspondence to Rui Shang .

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Shang, R. (2017). β-Arylation of Carboxamides Via Iron-Catalyzed C(sp3)–H Bond Activation. In: New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation. Springer Theses. Springer, Singapore. https://doi.org/10.1007/978-981-10-3193-9_10

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