Copper-Catalyzed 1,2-Amino Oxygenation of 1,3-Dienes: A Chemo-, Regio-, and Site-Selective Three-Component Reaction with <i>O</i>-Acylhydroxylamines and Carboxylic Acids

Hemric, Brett N.; Chen, Andy W.; Wang, Qiu

doi:10.1021/acscatal.9b03076

Cited by 64 publications

(30 citation statements)

References 45 publications

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“…Aminative difunctionalizations of alkenes installing tertiary amines are better developed compared to the installation of unprotected secondary amines [4–6, 16, 23h–j] . However, due to significant limitations in alkene scope, the discovery of a broadly applicable method remains desirable.…”

Section: Resultsmentioning

confidence: 99%

Design and Scalable Synthesis of N‐Alkylhydroxylamine Reagents for the Direct Iron‐Catalyzed Installation of Medicinally Relevant Amines**

et al. 2020

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Secondary and tertiary alkylamines are privileged substance classes that are often found in pharmaceuticals and other biologically active small molecules. Herein, we report their direct synthesis from alkenes through an aminative difunctionalization reaction enabled by iron catalysis. A family of ten novel hydroxylamine‐derived aminating reagents were designed for the installation of several medicinally relevant amine groups, such as methylamine, morpholine and piperazine, through the aminochlorination of alkenes. The method has excellent functional group tolerance and a broad scope of alkenes was converted to the corresponding products, including several drug‐like molecules. Besides aminochlorination, the installation of other functionalities through aminoazidation, aminohydroxylation and even intramolecular carboamination reactions, was demonstrated, further highlighting the broad potential of these new reagents for the discovery of novel amination reactions.

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Section: Resultsmentioning

confidence: 99%

Design and Scalable Synthesis of N‐Alkylhydroxylamine Reagents for the Direct Iron‐Catalyzed Installation of Medicinally Relevant Amines**

et al. 2020

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“…Column chromatography was performed on silica gel (200-300 mesh), eluting with ethyl acetate and petroleum ether. N-methoxybenzamide 21 and conjugated diene 22 were prepared according to the literature procedures.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Rh(III)-Catalyzed Tandem [4+2] Annulation To Construct Functional Dihydroisoquinolinones

Dong

Yang

2022

Synthesis

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“…In connection to the work on the Cu‐catalyzed amino etherification of alkenes, [18] Wang and co‐workers reported a relatively similar strategy that generated difunctionalized products in moderate yields (Scheme 7). [19] By comparison, the reactions in Scheme 5 and Scheme 7 totally occur through copper‐catalyzed amination of alkenes followed by nucleophilic addition of oxygen‐containing groups, like alcohols and carboxylic acids. The difference is that one is intramolecular cyclization and the other is intermolecular amination.…”

Section: Amines As Nitrogen Sourcesmentioning

confidence: 99%

Recent Advances in Copper‐Catalyzed C−N Bond Formation Involving N‐Centered Radicals

Zheng

et al. 2021

ChemSusChem

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C−N bonds are pervasive throughout organic‐based materials, natural products, pharmaceutical compounds, and agricultural chemicals. Considering the widespread importance of C−N bonds, the development of greener and more convenient ways to form C−N bonds, especially in late‐stage synthesis, has become one of the hottest research goals in synthetic chemistry. Copper‐catalyzed radical reactions involving N‐centered radicals have emerged as a sustainable and promising approach to build C−N bonds. As a chemically popular and diverse radical species, N‐centered radicals have been used for all kinds of reactions for C−N bond formation by taking advantage of their inherently incredible reactive flexibility. Copper is also the most abundant and economic catalyst with the most relevant activity for facilitating the synthesis of valuable compounds. Therefore, the aim of the present Review was to illustrate recent and significant advances in C−N bond formation methods and to understand the unique advantages of copper catalysis in the generation of N‐centered radicals since 2016. To provide an ease of understanding for the readers, this Review was organized based on the types of nitrogen sources (amines, amides, sulfonamides, oximes, hydrazones, azides, and tert‐butyl nitrite).

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Copper-Catalyzed 1,2-Amino Oxygenation of 1,3-Dienes: A Chemo-, Regio-, and Site-Selective Three-Component Reaction with O-Acylhydroxylamines and Carboxylic Acids

Cited by 64 publications

References 45 publications

Design and Scalable Synthesis of N‐Alkylhydroxylamine Reagents for the Direct Iron‐Catalyzed Installation of Medicinally Relevant Amines**

Design and Scalable Synthesis of N‐Alkylhydroxylamine Reagents for the Direct Iron‐Catalyzed Installation of Medicinally Relevant Amines**

Rh(III)-Catalyzed Tandem [4+2] Annulation To Construct Functional Dihydroisoquinolinones

Recent Advances in Copper‐Catalyzed C−N Bond Formation Involving N‐Centered Radicals

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