Ruthenium‐katalysierte <i>ortho</i>‐Alkylierung von Phenolen mit Alkoholen durch dehydratisierende Kupplung

Walton, James W.; Williams, Jonathan M. J.

doi:10.1002/ange.201206246

Angewandte Chemie

2012

DOI: 10.1002/ange.201206246

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Ruthenium‐katalysierte ortho‐Alkylierung von Phenolen mit Alkoholen durch dehydratisierende Kupplung

James W. Walton

Jonathan M. J. Williams

Abstract: Alkohol rein, Wasser raus: Phenole wurden in einer Ruthenium‐katalysierten ortho‐Alkylierung mit nichtaktivierten Alkoholen als Alkylierungsreagentien umgesetzt (siehe Schema; Cy=Cyclohexyl). Weil als einziges Nebenprodukt Wasser anfiel, ist diese Methode atomökonomischer und „grüner“ als klassische Verfahren zur C‐C‐Verknüpfung.

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Cited by 4 publications

References 30 publications

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Copper‐Catalyzed Dehydrative Cyclization of 1‐(2‐Hydroxyphenyl)propargyl Alcohols with P(O)H Compounds for the Synthesis of 2‐Phosphorylmethylbenzofurans

Zhang

Yang

et al. 2018

Adv Synth Catal

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A tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN)PF6]‐catalyzed dehydrative reaction of 1‐(2‐hydroxyphenyl)propargyl alcohols with diarylphosphine oxides has been developed to provide an efficient synthesis of phosphorylated benzofurans in good to high yields. In the presence of a catalytic amount of an organic base, a variety of H‐phosphonates and H‐phosphinates can also be employed as good substrates to produce the corresponding products in moderate yields. The reaction has significant economical and ecological advantages since the formation of a new C(sp3)–P bond and the benzofuran framework could both be achieved using an inexpensive copper catalyst with water produced as the sole by‐product. Some synthetic transformations of the product have also been demonstrated.magnified image

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Copper‐Catalyzed Dehydrative Cyclization of 1‐(2‐Hydroxyphenyl)propargyl Alcohols with P(O)H Compounds for the Synthesis of 2‐Phosphorylmethylbenzofurans

Zhang

Yang

et al. 2018

Adv Synth Catal

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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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Nitrogen, Phosphorus, and Sulfur Co‐Doped Hollow Carbon Shell as Superior Metal‐Free Catalyst for Selective Oxidation of Aromatic Alkanes

Yang

Huang

et al. 2016

Angewandte Chemie

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Metal-free heteroatom-doped carbocatalysts with ahigh surface area are desirable for catalytic reactions.Inthis study,w ef ound an efficient strategy to prepare nitrogen, phosphorus,and sulfur co-doped hollowcarbon shells (denote as NPS-HCS) with as urface area of 1020 m 2 g À1 .U sing ap oly(cyclotriphosphazene-co-4,4'-sulfonyldiphenol) (PZS) shell as carbon source and N, P, S-doping source,and the ZIF-67 core as structural template as well as extra N-doping source, NPS-HCS were obtained with ah igh surface area and superhydrophilicity.A ll these features render the prepared NPS-HCS asuperior metal-free carbocatalyst for the selective oxidation of aromatic alkanes in aqueous solution. This study provides ar eliable and facile route to prepare doped carbocatalysts with enhanced catalytic properties.

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Ruthenium‐katalysierte ortho‐Alkylierung von Phenolen mit Alkoholen durch dehydratisierende Kupplung

Cited by 4 publications

References 30 publications

Copper‐Catalyzed Dehydrative Cyclization of 1‐(2‐Hydroxyphenyl)propargyl Alcohols with P(O)H Compounds for the Synthesis of 2‐Phosphorylmethylbenzofurans

Copper‐Catalyzed Dehydrative Cyclization of 1‐(2‐Hydroxyphenyl)propargyl Alcohols with P(O)H Compounds for the Synthesis of 2‐Phosphorylmethylbenzofurans

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

Nitrogen, Phosphorus, and Sulfur Co‐Doped Hollow Carbon Shell as Superior Metal‐Free Catalyst for Selective Oxidation of Aromatic Alkanes

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Ruthenium‐katalysierte ortho‐Alkylierung von Phenolen mit Alkoholen durch dehydratisierende Kupplung

Cited by 4 publications

References 30 publications

Copper‐Catalyzed Dehydrative Cyclization of 1‐(2‐Hydroxyphenyl)propargyl Alcohols with P(O)H Compounds for the Synthesis of 2‐Phosphorylmethylbenzofurans

Copper‐Catalyzed Dehydrative Cyclization of 1‐(2‐Hydroxyphenyl)propargyl Alcohols with P(O)H Compounds for the Synthesis of 2‐Phosphorylmethylbenzofurans

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

Nitrogen, Phosphorus, and Sulfur Co‐Doped Hollow Carbon Shell as Superior Metal‐Free Catalyst for Selective Oxidation of Aromatic Alkanes

Contact Info

Product

Resources

About

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