Cu(OAc)<sub>2</sub>-catalyzed hydrazination of cyclopropanols and late-stage transformation to 4,5-dihydropyrazoles

Zhang, Kui; Wei, Cong; Yao, Yueyang; Song, Liangliang; Jin, Junhong; Cai, Lingchao

doi:10.1039/d2nj05989d

Cited by 4 publications

(1 citation statement)

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“…As our continuous interest in C(sp 3 )–H functionalization of peptides (Scheme d) , and fluorine chemistry, we herein describe a novel transformation that includes the organo-photoredox-catalyzed C(sp 3 )–H difluoroallylation of glycine and glycine-containing peptides with α-trifluoromethyl alkenes through intermolecular α-amino carbanion addition (Scheme e), producing the structurally diverse β- gem -difluoroalkyl glycine derivatives in moderate to good yields. − …”

Section: Introductionmentioning

confidence: 99%

Organo-Photoredox Catalyzed gem-Difluoroallylation of Glycine and Glycine Residue in Peptides

Lin,

Shan,

et al. 2024

J. Org. Chem.

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An organo-photoredox catalyzed gem-difluoroallylation of glycine with α-trifluoromethyl alkenes via direct C(sp 3 )−H functionalization of glycine and C−F bond activation of αtrifluoromethyl alkenes has been described. As a consequence, a broad range of gem-difluoroalkene-containing unnatural amino acids are afforded in moderate to excellent yields. This reaction exhibits multiple merits such as readily available starting materials, broad substrate scope, and mild reaction conditions. The feasibility of this reaction has been highlighted by the late-stage modification of several peptides as well as the improved in vitro antifungal activity of compound 3v toward Valsa mali compared to that with commercial azoxystrobin.

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Section: Introductionmentioning

confidence: 99%

Organo-Photoredox Catalyzed gem-Difluoroallylation of Glycine and Glycine Residue in Peptides

Lin,

Shan,

et al. 2024

J. Org. Chem.

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Catalytic Deoxygenative Reduction of Hydrazides to Hydrazines via B(C₆F₅)₃‐Catalyzed Hydrosilylation

Wang,

Yang,

Luo

et al. 2023

Adv Synth Catal

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The catalytic deoxygenative reduction of hydrazides to the corresponding alkyl hydrazine with PhSiH3 via B(C6F5)3‐catalyzed hydrosilylation is reported. This metal‐free protocol is compatible with various acylhydrazides and diacylhydrazides, giving rise to a variety of structurally diverse alkyl hydrazine products in 63–95% yields. The proper selection of borane catalyst and hydrosilane reductant is essential for catalysis. Mechanistic investigations reveal that the reaction involves a hydrazone intermediate.

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Ligand‐Tailored Divergence of Copper‐Catalyzed Aerobic Oxidation of Cyclopropanols. Application to the Practical Synthesis of β‐Aminoketones and β‐Enaminones

Zavalinich,

Elek,

Vailhé

et al. 2024

Adv Synth Catal

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The aerobic ring‐opening oxidation of cyclopropanols catalyzed by copper complexes was systematically investigated, with a focus on the effect of nitrogen ligands on the distribution of oxidation products. This study led to the development of a new synthesis of β‐aminoketones and β‐enaminones from cyclopropanols, where product specificity is tuned through ligand and solvent selection. β‐Aminoketones were prepared in 34–99% yields by copper(II) acetate‐catalyzed aerobic oxidation of cyclopropanols in the presence of nucleophilic secondary aliphatic amines. In contrast, bipyridine‐ligated copper catalysts resulted in the generation of β‐enaminones in 36–86% yields, presumably via the Kornblum‐DeLaMare rearrangement of intermediate 1,2‐dioxolanes

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Cu(OAc)₂-catalyzed hydrazination of cyclopropanols and late-stage transformation to 4,5-dihydropyrazoles

Abstract: A low-cost and commercially available Cu(OAc)2 catalyzed hydrazination of cyclopropyl alcohols is developed. This procedure featured mild reaction conditions and good to excellent yields, providing a feasible method for the...

Cited by 4 publications

References 41 publications

Organo-Photoredox Catalyzed gem-Difluoroallylation of Glycine and Glycine Residue in Peptides

Organo-Photoredox Catalyzed gem-Difluoroallylation of Glycine and Glycine Residue in Peptides

Catalytic Deoxygenative Reduction of Hydrazides to Hydrazines via B(C₆F₅)₃‐Catalyzed Hydrosilylation

Ligand‐Tailored Divergence of Copper‐Catalyzed Aerobic Oxidation of Cyclopropanols. Application to the Practical Synthesis of β‐Aminoketones and β‐Enaminones

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Cu(OAc)2-catalyzed hydrazination of cyclopropanols and late-stage transformation to 4,5-dihydropyrazoles

Abstract: A low-cost and commercially available Cu(OAc)2 catalyzed hydrazination of cyclopropyl alcohols is developed. This procedure featured mild reaction conditions and good to excellent yields, providing a feasible method for the...

Cited by 4 publications

References 41 publications

Organo-Photoredox Catalyzed gem-Difluoroallylation of Glycine and Glycine Residue in Peptides

Organo-Photoredox Catalyzed gem-Difluoroallylation of Glycine and Glycine Residue in Peptides

Catalytic Deoxygenative Reduction of Hydrazides to Hydrazines via B(C6F5)3‐Catalyzed Hydrosilylation

Ligand‐Tailored Divergence of Copper‐Catalyzed Aerobic Oxidation of Cyclopropanols. Application to the Practical Synthesis of β‐Aminoketones and β‐Enaminones

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Cu(OAc)₂-catalyzed hydrazination of cyclopropanols and late-stage transformation to 4,5-dihydropyrazoles

Catalytic Deoxygenative Reduction of Hydrazides to Hydrazines via B(C₆F₅)₃‐Catalyzed Hydrosilylation