Cp*Co(III)-Catalyzed Annulations of 2-Alkenylphenols with CO: Mild Access to Coumarin Derivatives

Liu, Xu‐Ge; Zhang, Shang‐Shi; Jiang, Chun‐Yong; Wu, Jia‐Qiang; Li, Qingjiang; Wang, Honggen

doi:10.1021/acs.orglett.5b02728

Cited by 134 publications

(37 citation statements)

References 76 publications

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“…In addition to nitrogen based 6‐membered heterocycles, oxygen based heterocycles such as coumarin and chromenes were achieved employing Co(III) catalysis. In 2015, Wang and co‐workers demonstrated a Cp*Co(III)‐catalyzed synthesis of coumarins through cyclocarbonylation of 2‐vinylphenols with carbon monoxide in presence of stoichiometric amount of both Ag 2 CO 3 and Cu(OAc) 2 ⋅ H 2 O (Scheme a) . Regardless of the electronic nature of the substitution wide ranges of ortho‐vinylphenols were converted coumarin derivatives under the developed reaction conditions in good yield.…”

Section: Construction Of Carbo/heterocyclesmentioning

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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Section: Construction Of Carbo/heterocyclesmentioning

confidence: 99%

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

Ghorai¹,

Anbarasan²

2019

Asian J Org Chem

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“…More recently, Wang et al described a rather mild cyclocarbonylation of 2-vinylphenols 37 in the presence of Cp*Co(III) catalyst ( Scheme 7 ) [ 73 ]. With Ag 2 CO 3 and Cu(OAc) 2 ·H 2 O as co-oxidants, the reaction could sufficiently be proceeded under a balloon pressure of CO. A plausible mechanism of the reaction is depicted in Scheme 7 .…”

Section: Cyclocarbonylation and Cyclocarboxylation Toward Central mentioning

confidence: 99%

Recent Advances in Synthesis of 4-Arylcoumarins

et al. 2018

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4-Arylcoumarins (4-aryl-2H-1-benzopyran-2-one), also known as neoflavones, comprise a minor subclass of naturally occurring flavonoids. Because of their broad-spectrum biological activities, arylcoumarins have been attracting the attention of the organic and medicinal chemistry communities, and are considered as an important privileged scaffold. Since the development of Pechmann condensation, a classical acid-catalyzed condensation between phenol and β-keto-carboxylic acid, several versatile and efficient synthetic approaches for 4-arylcoumarins have been reported. This review summarizes recent advances in the synthesis of the 4-arylcoumarin scaffold by classifying them based on the final bond-formation type. In particular, synthetic methods executed under mild and highly efficient conditions, such as solvent-free reactions and transition metal catalysis, are highlighted.

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“…Verwandte Carbonylierungen, die zu wertvollen Cumarinen führen, können auch durch eine Rh‐katalysierte Reaktion von ortho ‐Hydroxystyrolen und Kohlenmonoxid erzielt werden (Schema ) . Kürzlich wurde diese Umwandlung mit einem Co III ‐Katalysator durchgeführt …”

Section: Anellierungen Durch C‐h‐aktivierung Migratorische Insertiounclassified

Metallkatalysierte Anellierungen durch Aktivierung und Spaltung von C‐H‐Bindungen

2016

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Die außerordentliche Zunahme der Zahl katalytischer Umwandlungen über eine metallvermittelte Aktivierung von zuvor als inert angesehenen C‐H‐Bindungen zeugt von einem grundlegenden Wandel auf dem Gebiet der Synthesechemie. Während die meisten Reaktionen mit C‐H‐Aktivierung einfache Funktionalisierungen oder Additionen sind, wuchs in den letzten Jahren das Interesse an verwandten Umwandlungen, die formal als Cycloadditionsprozesse betrachtet werden können. Diese Reaktionen sind besonders für die Synthese vielversprechend, da sie die schnelle und nachhaltige Umwandlung leicht zugänglicher Substrate in wertvolle cyclische Produkte ermöglichen. In vielen Fällen entstehen bei diesen Anellierungsreaktionen metallacyclische Intermediate, die denen der herkömmlichen metallkatalysierten Cycloadditionen ungesättigter Vorstufen ähneln.

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Cp*Co(III)-Catalyzed Annulations of 2-Alkenylphenols with CO: Mild Access to Coumarin Derivatives

Cited by 134 publications

References 76 publications

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

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

Recent Advances in Synthesis of 4-Arylcoumarins

Metallkatalysierte Anellierungen durch Aktivierung und Spaltung von C‐H‐Bindungen

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Cp*Co(III)-Catalyzed Annulations of 2-Alkenylphenols with CO: Mild Access to Coumarin Derivatives

Cited by 134 publications

References 76 publications

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

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

Recent Advances in Synthesis of 4-Arylcoumarins

Metallkatalysierte Anellierungen durch Aktivierung und Spaltung von C‐H‐Bindungen

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

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