Fundamental Aspects of the Metal‐Catalyzed C–H Bond Functionalization by Diazocarbenes: Guiding Principles for Design of Catalyst with Non‐redox‐Active Metal (Such as Ca) and Non‐Innocent Ligand

Varela‐Álvarez, Adrián; Musaev, Djamaladdin G.

doi:10.1002/9783527678211.ch2

Understanding Organometallic Reaction Mechanisms and Catalysis 2014

DOI: 10.1002/9783527678211.ch2

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Fundamental Aspects of the Metal‐Catalyzed C–H Bond Functionalization by Diazocarbenes: Guiding Principles for Design of Catalyst with Non‐redox‐Active Metal (Such as Ca) and Non‐Innocent Ligand

Adrián Varela‐Álvarez

Djamaladdin G. Musaev

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2019

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One‐Electron Reduction of 2‐Mono(2,6‐diisopropylphenylimino)acenaphthene‐1‐one (dpp‐mian)

Lukoyanov

Ulivanova

Razborov

et al. 2019

Chemistry A European J

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The electrochemical characteristics of 2‐mono(2,6‐diisopropylphenylimino)acenaphthene‐1‐one (dpp‐mian) have been investigated. One‐electron reduction of dpp‐mian involves the iminoketone fragment, which is revealed by the EPR spectrum obtained after the electrolysis of the dpp‐mian solution in tetrahydrofuran (THF). The reduction of dpp‐mian with one equivalent of metallic potassium leads to a similar EPR spectrum. The sodium complex [(dpp‐mian)Na(dme)]2 (1) produces an EPR signal with hyperfine coupling on the nitrogen atom of the iminoketone fragment of the dpp‐mian ligand. Dpp‐mian can also be reduced in a one‐electron process by SnCl2×(dioxane). In this case, complex (dpp‐mian)2SnCl2 (2) is formed, with the tin atom displaying an oxidation state of +4. Tin(II) chloride dihydrate, SnCl2×2(H2O), also reduces dpp‐mian, but the two ligands bound to tin in the product form a new carbon–carbon bond between the ketone moieties of the dpp‐mian monoanions to form complex (bis‐dpp‐mian)HSnCl3 (3). Metallic tin reduces dpp‐mian to form the (bis‐dpp‐mian)2Sn (4) species. Compounds 1–4 were characterized by X‐ray diffraction.

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One‐Electron Reduction of 2‐Mono(2,6‐diisopropylphenylimino)acenaphthene‐1‐one (dpp‐mian)

Lukoyanov

Ulivanova

Razborov

et al. 2019

Chemistry A European J

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show abstract

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Fundamental Aspects of the Metal‐Catalyzed C–H Bond Functionalization by Diazocarbenes: Guiding Principles for Design of Catalyst with Non‐redox‐Active Metal (Such as Ca) and Non‐Innocent Ligand

Cited by 1 publication

References 125 publications

One‐Electron Reduction of 2‐Mono(2,6‐diisopropylphenylimino)acenaphthene‐1‐one (dpp‐mian)

One‐Electron Reduction of 2‐Mono(2,6‐diisopropylphenylimino)acenaphthene‐1‐one (dpp‐mian)

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