Transition metal catalyzed hydroarylation of olefins using unactivated substrates: Recent developments and challenges

Andreatta, Jeremy R.; McKeown, Bradley A.; Gunnoe, T. Brent

doi:10.1016/j.jorganchem.2010.09.030

Cited by 113 publications

(81 citation statements)

References 51 publications

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“…[58] Ihre wohlbekannten Nachteile haben jedoch die Entwicklung alternativer, übergangsmetallkatalysierter C-HAlkylierungsmethoden, wie direkten Alkylierungen, [59,60] dehydrierenden Kupplungen [61] oder Olefin-Hydroarylierungen, [62] bewirkt. Ein wertvolles Beispiel, das in diesem Zusammenhang hervorgehoben werden soll, ist die von Michael et al entwickelte Carboaminierung.…”

Section: Alkylierung Einfacher Areneunclassified

Ohne dirigierende Gruppen: übergangsmetallkatalysierte C‐H‐Aktivierung einfacher Arene

et al. 2012

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Der Einsatz von koordinierenden Gruppen als dirigierende Gruppen ist eine zuverlässige Methode zur Kontrolle von Reaktivität und Selektivität bei der Aktivierung von Aryl‐C‐H‐Bindungen. Im Hinblick auf die Anwendbarkeit von C‐H‐Aktivierungen in der Synthese besteht derzeit ein großes Interesse daran, Reaktionen zu entwickeln, in denen völlig auf dirigierende Gruppen verzichtet werden kann und somit die Funktionalisierung einfacher Benzolderivate möglich wird. Dieser Ansatz erfordert jedoch neue Strategien zur Reaktivitäts‐ und Selektivitätskontrolle. In diesem Kurzaufsatz werden aktuelle Fortschritte in dem noch jungen Gebiet der nicht‐chelatvermittelten C‐H‐Aktivierung diskutiert, wobei einige inspirierende Beispiele zur Reaktivitäts‐ und Selektivitätsinduktion hervorgehoben werden.

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Section: Alkylierung Einfacher Areneunclassified

Ohne dirigierende Gruppen: übergangsmetallkatalysierte C‐H‐Aktivierung einfacher Arene

et al. 2012

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“…Several examples of catalytic C–H activation/functionalization reactions involving homogeneous transition metal complexes have emerged in the past two decades . Most germane to the discussion herein is the hydroarylation of olefins, which is defined as the addition of an aromatic C–H bond across the C=C bond of an unsaturated substrate to exclusively prepare a single mono‐alkylated aromatic product . While heteroaromatic substrates,, functionalized olefins,, and C=X (X = O or NR) have been explored,, the discussion below will be limited to the mechanistic investigation of hydrophenylation of unactivated olefins (e.g., ethylene, propylene, and 1‐hexene).…”

Section: Introductionmentioning

confidence: 99%

Transition Metal Mediated C–H Activation and Functionalization: The Role of Poly(pyrazolyl)borate and Poly(pyrazolyl)alkane Ligands

et al. 2016

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“…substituted alkenes and alkynes is a powerful technique in organic synthesis. This method provides highly atom/step economy and has various advantages over the conventional alkylation through Friedel‐Crafts‐type reaction and direct addition of organometallic reagents into α , β ‐unsaturated carbonyl compounds . Although, significant advancement has occurred in precious transition metal catalyzed C−H bond addition into carbon‐carbon multiple bond, last few years high valent Cp*Co(III)‐catalysts has emerged as efficient system in organic synthesis for construction of C−C bond through C−H bond functionalization.…”

Section: Construction Of C−c Bondmentioning

confidence: 99%

Developments in Cp*Co^III‐Catalyzed C−H Bond Functionalizations

Ghorai¹,

Anbarasan²

2019

Asian J Org Chem

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Transition-metal-catalyzed CÀ H bond functionalization has emerged as a powerful tool in contemporary organic synthesis. In this aspect, precious metal-based high-valent catalysts have been extensively studied. In the past decade, earth-abundant high-valent Cp*Co(III)-catalysts have emerged as a promising alternative to the expensive transition metals, providing unique selectivity and reactivity. In this Minireview, we summarized important progresses in the area of Cp*Co (III)-catalyzed CÀ H bond functionalization until 2017.[a] Mr. . Alkylation of CÀ H bonds with activated alkene. Scheme 3. Alkylation of CÀ H bonds with activated alkene. Scheme 4. Alkylation of CÀ H bonds with maleimides.Scheme 5. Alkylation of CÀ H bonds of (hetero)arene with maleimide. Scheme 6. Alkylation of CÀ H bonds with unactivated alkenes. Scheme 7. Allylation of CÀ H bonds with allyl carbonates. . Allylation of CÀ H bonds with allyl acetate. Scheme 9. Allylation of CÀ H bonds of arenes with allyl carbonates. Scheme 10. Allylation of CÀ H bonds with allyl alcohol. Scheme 11. Cobalt catalyzed allylation using allyl alcohol. Scheme 12. Cobalt catalyzed allylation with activated allylating reagent. . Cobalt catalyzed selective addition of C2À H bond to C=N bond. Scheme 18. Cobalt catalyzed selective addition of CÀ H bond to isocyanate. Scheme 19. Cobalt(III)-catalyzed aryl and alkenyl CÀ H aminocarbonylation. Scheme 20. Cobalt catalyzed hydroarylation to ketenimines. Scheme 21. Cobalt catalyzed synthesis of pyrroloindolones. Scheme 22. Cobalt catalyzed alkenylation through hydroarylation to alkyne. Co(III)-catalyzed alkenylation. Scheme 24. Cobalt catalyzed alkenylation of heterocyclic moiety. Scheme 25. Cp*Co III -Catalyzed branch-selective hydroarylation of alkynes. Scheme 26. Cobalt catalyzed C(sp 3 )À H alkenylation. . Cobalt(III)-catalyzed amidation with dioxazolone. Scheme 40. Mechanism of cobalt catalyzed amidation with dioxazolone. Scheme 41. Cobalt(III)-catalyzed CÀ H bond amidation using dioxazolone.

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Transition metal catalyzed hydroarylation of olefins using unactivated substrates: Recent developments and challenges

Cited by 113 publications

References 51 publications

Ohne dirigierende Gruppen: übergangsmetallkatalysierte C‐H‐Aktivierung einfacher Arene

Ohne dirigierende Gruppen: übergangsmetallkatalysierte C‐H‐Aktivierung einfacher Arene

Transition Metal Mediated C–H Activation and Functionalization: The Role of Poly(pyrazolyl)borate and Poly(pyrazolyl)alkane Ligands

Developments in Cp*Co^III‐Catalyzed C−H Bond Functionalizations

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Transition metal catalyzed hydroarylation of olefins using unactivated substrates: Recent developments and challenges

Cited by 113 publications

References 51 publications

Ohne dirigierende Gruppen: übergangsmetallkatalysierte C‐H‐Aktivierung einfacher Arene

Ohne dirigierende Gruppen: übergangsmetallkatalysierte C‐H‐Aktivierung einfacher Arene

Transition Metal Mediated C–H Activation and Functionalization: The Role of Poly(pyrazolyl)borate and Poly(pyrazolyl)alkane Ligands

Developments in Cp*CoIII‐Catalyzed C−H Bond Functionalizations

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Developments in Cp*Co^III‐Catalyzed C−H Bond Functionalizations