Copper-Catalyzed Oxidative Difunctionalization of Terminal Unactivated Alkenes

Hussain, Muhammad Ijaz; Feng, Yangyang; Hu, Liangzhen; Deng, Qingfu; Zhang, Xiaohui; Xiong, Yan

doi:10.1021/acs.joc.8b00729

Cited by 30 publications

(12 citation statements)

References 78 publications

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“…In 2018, metal-catalyzed free-radical oxidative oxyazidation methods for terminal alkenes have been reported by various groups to access a-azidoketones by utilizing molecular oxygen. Singh et al 104 used MnO 2 catalyst for aryl enol acetates as the substrate, whereas the Xiong group 105 utilized the Cu(OTf) 2 catalyst for styrenes. However, these methods are not generalized in terms of substrate scope and require metal catalysts.…”

Section: Functionalization Of Alkenesmentioning

confidence: 99%

Chemical versatility of azide radical: journey from a transient species to synthetic accessibility in organic transformations

Shee

Singh

2022

Chem. Soc. Rev.

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Section: Functionalization Of Alkenesmentioning

confidence: 99%

Chemical versatility of azide radical: journey from a transient species to synthetic accessibility in organic transformations

Shee

Singh

2022

Chem. Soc. Rev.

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“…In 2018, Xiong and co‐workers proposed an environmentally friendly Cu(OTf) 2 ‐catalyzed radical oxidative difunctionalization method for the synthesis of ketoazides from terminal alkenes in the presence of molecular oxygen and TMSN 3 in MeCN at room temperature (Scheme 42). [56] Comparably, O 2 was used in both of these methods. Mechanistically, a combined use of 1/4 O 2 , HOAC and CuOAc could reproduce the Cu(OAc) 2 , demonstrating the simple role of oxygen in the reaction [55] .…”

Section: Azides 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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“…Molecular oxygen is not only an oxidant but also O atom source in this reaction, as shown by 18 O-labeling studies ( Table 3, entry 4). 62 In 2019, the Li group demonstrated an azidoperoxidation of styrenes with TMSN 3 and TBHP to generate a series of -azido peroxide derivatives (Table 3, entry 5). 63…”

Section: Tmsn 3 As a N-centered Radical Sourcementioning

confidence: 99%

Radical-Mediated Difunctionalization of Styrenes

Bao¹,

Li²,

Jiang³

et al. 2019

Synthesis

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Styrene, an extremely important compound in the chemical industry, is mainly produced by the dehydrogenation or oxidative dehydrogenation of ethylbenzene. Transformation of this raw organic material to more useful fine organic chemicals is a very significant topic. Recently, the radical difunctionalization of styrene has become a powerful and efficient tool for organic synthesis. This strategy can introduce two substituents into a styrene molecule in one step via addition to the C=C bond, enhancing the molecular complexity in a single operation with good selectivity and wide functional group compatibility.1 Introduction2 C-Centered Radicals3 CF3 and Other Polyfluoroalkyl Radicals4 N-Centered Radicals5 P-Centered Radicals6 O-Centered Radicals7 S-Centered Radicals8 Other-Atom-Centered Radicals9 Conclusion and Perspective

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Copper-Catalyzed Oxidative Difunctionalization of Terminal Unactivated Alkenes

Cited by 30 publications

References 78 publications

Chemical versatility of azide radical: journey from a transient species to synthetic accessibility in organic transformations

Chemical versatility of azide radical: journey from a transient species to synthetic accessibility in organic transformations

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

Radical-Mediated Difunctionalization of Styrenes

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