Ligand effects in the rhodium-catalyzed addition of alkynes to aldehydes and diketones. Modification of the β-diketonate ligand

Dhondi, Pawan K.; Carberry, Patrick; Chisholm, John D.

doi:10.1016/j.tetlet.2007.10.010

Cited by 10 publications

(1 citation statement)

References 25 publications

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“…General methods: All reagents and solvents were obtained from commercial sources, and were used without further purification unless otherwise www.chemeurj.org (13) were synthesized according to literature procedures. [7,17,21,27] 1,3-Di(4-methoxy-A C H T U N G T R E N N U N G phenyl)A C H T U N G T R E N N U N G propane-1,3-dione and 1,3-diphenylpropane-1,3-dione were purchased from TCI and ACROS, respectively, and were used as received. Dry acetonitrile was prepared according to a literature procedure [28] and was used in the metal complex syntheses.…”

Section: Methodsmentioning

confidence: 99%

Photochemically Initiated Oxidative Carbon–Carbon Bond‐Cleavage Reactivity in Chlorodiketonate Ni^II Complexes

Allpress

Arif

Houghton

et al. 2011

Chemistry A European J

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Three mononuclear Ni(II) complexes containing a 2-chloro-1,3-diketonate ligand and supported by the 6-Ph(2)TPA chelate, as well as analogues that lack the 2-chloro substituent on the β-diketonate ligand, have been prepared and characterized. Upon irradiation at 350 nm under aerobic conditions, complexes containing the 2-chloro-substituted ligands undergo reactions to generate products resulting from oxidative cleavage, α-cleavage, and radical-derived reactions involving the 2-chloro-1,3-diketonate ligand. Mechanistic studies suggest that the oxidative cleavage reactivity, which leads to the production of carboxylic acids, is a result of the formation of superoxide, which occurs through reaction of reduced nickel complexes with O(2). The presence of the 2-chloro substituent was found to be a prerequisite for oxidative carbon-carbon bond-cleavage reactivity, as complexes lacking this functional group did not undergo these reactions following prolonged irradiation. The approach toward investigating the oxidative reactivity of metal β-diketonate species outlined herein has yielded results of relevance to the proposed mechanistic pathways of metalloenzyme-catalyzed β-diketonate oxidative cleavage reactions.

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Section: Methodsmentioning

confidence: 99%

Photochemically Initiated Oxidative Carbon–Carbon Bond‐Cleavage Reactivity in Chlorodiketonate Ni^II Complexes

Allpress

Arif

Houghton

et al. 2011

Chemistry A European J

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Aspects of the Energetics of Metal β‐Diketonates and their Derivatives

Zeiger

Liebman

Ponikvar‐Svet

2017

Patai's Chemistry of Functional Groups

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In this chapter, we will discuss diverse aspects of the energetics of metal β‐diketonates and their derivatives. By “energetics” we mean thermochemical and related studies, and so we include enthalpies of reaction and of formation as well as equilibrium measurements and stability constants. We will also discuss the gain or loss of an electron, and therefore consider ionization potentials, electron affinities, and electrochemical potentials. By metal β‐diketonates and derivatives we mean, most generally, species with a substructure of the type [M(dik) n ], where dik (β‐diketonato) is an organic monovalent anion of structure (RC(X)C(R 1 )C(O)R 2 ) − and M is an arbitrary metal. For completeness and additional insights, in this chapter we will also consider M to be virtually all elements (nonmetal, metalloid, or metal), and eventually we will include hydrogen.

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Reactions of Aldehydes and Ketones and their Derivatives

Knipe¹

2007

Organic Reaction Mechanisms Series

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Ligand effects in the rhodium-catalyzed addition of alkynes to aldehydes and diketones. Modification of the β-diketonate ligand

Cited by 10 publications

References 25 publications

Photochemically Initiated Oxidative Carbon–Carbon Bond‐Cleavage Reactivity in Chlorodiketonate Ni^II Complexes

Photochemically Initiated Oxidative Carbon–Carbon Bond‐Cleavage Reactivity in Chlorodiketonate Ni^II Complexes

Aspects of the Energetics of Metal β‐Diketonates and their Derivatives

Reactions of Aldehydes and Ketones and their Derivatives

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Ligand effects in the rhodium-catalyzed addition of alkynes to aldehydes and diketones. Modification of the β-diketonate ligand

Cited by 10 publications

References 25 publications

Photochemically Initiated Oxidative Carbon–Carbon Bond‐Cleavage Reactivity in Chlorodiketonate NiII Complexes

Photochemically Initiated Oxidative Carbon–Carbon Bond‐Cleavage Reactivity in Chlorodiketonate NiII Complexes

Aspects of the Energetics of Metal β‐Diketonates and their Derivatives

Reactions of Aldehydes and Ketones and their Derivatives

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Product

Resources

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Photochemically Initiated Oxidative Carbon–Carbon Bond‐Cleavage Reactivity in Chlorodiketonate Ni^II Complexes

Photochemically Initiated Oxidative Carbon–Carbon Bond‐Cleavage Reactivity in Chlorodiketonate Ni^II Complexes