Palladium-catalyzed C–C bond cleavage of <i>N</i>-cyclopropyl acylhydrazones

Fujioka, Hiroki; Yasui, Motohiro; Hamada, Shohei; Fukumi, Kohei; Takeda, Norihiko; Kobayashi, Yusuke; Furuta, Takumi; Ueda, Masafumi

doi:10.1039/d4ob00349g

Org. Biomol. Chem.

2024

DOI: 10.1039/d4ob00349g

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Palladium-catalyzed C–C bond cleavage of N-cyclopropyl acylhydrazones

Hiroki Fujioka,

Motohiro Yasui,

Shohei Hamada

et al.

Abstract: Pd-catalyzed C–C bond cleavage reaction of N-cyclopropyl acylhydrazones, followed by cycloisomerization to yield pyrazoles, has been developed. Control experiments and DFT calculations suggest that β-carbon elimination of a stable 6-membered...

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Palladium‐Catalyzed Synthesis of 1‐Alkyl‐5‐Arylpyrazoles: The Auto‐Tandem Catalysis for C−C Bond Cleavage/Heck Arylation

Fujioka,

Yasui,

Hamada

et al. 2024

Asian J Org Chem

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The regioselective synthesis of 1‐alkyl‐5‐arylpyrazoles, which are potential drug candidates, has been difficult to achieve thus far. In this study, we developed an auto‐tandem Pd‐catalyzed C–C bond cleavage/Heck arylation of N‐cyclopropylhydrazones followed by cycloisomerization to afford diverse 1‐alkyl‐5‐arylpyrazoles. This step‐economical synthesis involves the cleavage of two C–H bonds and one C–C bond as well as the incorporation of directing groups. The identification of the reaction intermediates indicated an auto‐tandem catalytic pathway. The further transformation of products to 1,4,5‐substituted pyrazole and functional group transformations were carried out.

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Palladium‐Catalyzed Synthesis of 1‐Alkyl‐5‐Arylpyrazoles: The Auto‐Tandem Catalysis for C−C Bond Cleavage/Heck Arylation

Fujioka,

Yasui,

Hamada

et al. 2024

Asian J Org Chem

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show abstract

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Palladium-catalyzed C–C bond cleavage of N-cyclopropyl acylhydrazones

Abstract: Pd-catalyzed C–C bond cleavage reaction of N-cyclopropyl acylhydrazones, followed by cycloisomerization to yield pyrazoles, has been developed. Control experiments and DFT calculations suggest that β-carbon elimination of a stable 6-membered...

Cited by 1 publication

References 65 publications

Palladium‐Catalyzed Synthesis of 1‐Alkyl‐5‐Arylpyrazoles: The Auto‐Tandem Catalysis for C−C Bond Cleavage/Heck Arylation

Palladium‐Catalyzed Synthesis of 1‐Alkyl‐5‐Arylpyrazoles: The Auto‐Tandem Catalysis for C−C Bond Cleavage/Heck Arylation

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