Cp*Co(<scp>iii</scp>)-catalyzed C–H amination/annulation cascade of sulfoxonium ylides with anthranils for the synthesis of indoloindolones

Aher, Yogesh N.; Pawar, Amit B.

doi:10.1039/d1cc02817k

Cited by 21 publications

(10 citation statements)

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“…Further, intermolecular aldol condensation of indolone intermediate VIII produces the desired tetracyclic indoloindolone derivative (Scheme 96). [140] …”

Section: Transformations Of Isoxazoles Via Tm‐catalyzed Ring Opening ...mentioning

confidence: 99%

“…In 2021, Pawar and Aher demonstrated a cobalt‐catalyzed C−H amination followed by annulation reaction of sulfoxonium ylides with anthranils affording indoloindolones (Scheme 96). [140] In this reaction, the anthranil was effectively utilized as an aminating agent and the aldehyde functionality of anthranils was exploited for cascade intramolecular aldol condensation to afford a useful indole–indolone scaffold.…”

Section: Transformations Of Isoxazoles Via Tm‐catalyzed Ring Opening ...mentioning

confidence: 99%

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Transition Metal‐Mediated Functionalization of Isoxazoles: A Review

2021

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Isoxazoles are an important class of heterocycles with nitrogen and oxygen in a 1,2-relationship. They find wide applications in synthetic organic chemistry and are part of several drug molecules. Since the last two decades, great progress has been achieved in the synthesis and functionalization of isoxazoles, in which transition metal catalysis played a pivotal role towards achieving this goal. In particular, the transition metal (TM)-mediated site-selective functionalizations of isoxazoles which retain the pharmacologically and synthetically valuable isoxazole skeleton, are highly appealing. This comprehensive review is solely dedicated to the TM-mediated functionalization of isoxazoles, wherein we have included isoxazoles as directing groups (DG) for TM-catalyzed CÀ H functionalization reactions, TM-catalyzed direct CÀ H functionalization, along with cross-coupling reactions of isoxazoles, TM-catalyzed annulation reactions of isoxazoles and finally ring-opening reactions of isoxazoles under TMcatalysis are also discussed. Also, incorporated are discussions on reaction designs, their advantages and limitations, mechanistic details and challenges that need to be addressed to inspire synthetic organic and medicinal chemists to explore new reaction arenas and make use of this key scaffold.Scheme 1. Synthetic approaches for functionalized isoxazoles.Scheme 2. Functionalization of isoxazoles via the 4-isoxazolyl anion species.

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“…Further, intermolecular aldol condensation of indolone intermediate VIII produces the desired tetracyclic indoloindolone derivative (Scheme 96). [140] …”

Section: Transformations Of Isoxazoles Via Tm‐catalyzed Ring Opening ...mentioning

confidence: 99%

Section: Transformations Of Isoxazoles Via Tm‐catalyzed Ring Opening ...mentioning

confidence: 99%

Transition Metal‐Mediated Functionalization of Isoxazoles: A Review

2021

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“…Taking advantage of the in situ generated carbonyl groups (Scheme 1a), the following annulations towards azacycles could be realized in a one-pot fashion. Based on this, Rh-, 3 Au-, 4 Pd-, 5 Ag-, 6 Co-, 7 and Cu-based catalysts 8 have been applied to construct a variety of downstream azacycles from anthranils. 9…”

Section: Introductionmentioning

confidence: 99%

Synthesis of acridinesviacopper-catalyzed amination/annulation cascades between arylboronic acids and anthranils

Yuge

2022

Org. Biomol. Chem.

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“…Numerous interesting examples of the use of [Cp*Co(CO)I 2 ] were reported in terminal couplings and heterocycle formation. − For bond activations through novel synthetic routes, discovering more efficient and profitable methods of using the various resources, reducing costs, and promoting the use of [Cp*Co(CO)I 2 ] is highly desirable. Although several mechanistic and computational studies have been carried out, − the appropriate choice of various solvents and additives, the reaction time, and the temperature remain very important.…”

Section: Introductionmentioning

confidence: 99%

Data-Driven Analysis of Reactions Catalyzed by [CoCp*(CO)I₂]

2022

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The combination of the [Cp*Co(CO)I 2 ] catalyst with various additives and solvents at different temperatures for different durations has led to a considerable increase in the amount of research regarding the catalysis of C−H functionalization via high-valent Co, owing to the unique reactivity of the catalyst. Our study presents, for the first time, a data-driven approach toward reported reactions catalyzed using [Cp*Co-(CO)I 2 ]. We analyze distinct solvents, additives, reaction times, temperatures, and directing groups with their associated mean yields, which accelerates the screening process in the laboratory to yield favorable combinations. We demonstrate the effects of reaction conditions and directing groups on the reaction performance by integrating data from the reaction. Additionally, we examine the reactions based on their yields using principal component analysis and the t-stochastic neighbor embedding method. These exploratory investigations may be very useful for synthetic chemists as a starting point in catalytic studies.

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Cp*Co(iii)-catalyzed C–H amination/annulation cascade of sulfoxonium ylides with anthranils for the synthesis of indoloindolones

Abstract: Cp*Co(III)-catalyzed [4+1] annulation of sulfoxonium ylides with anthranils has been developed for the synthesis of indole-indolone scaffolds. The dual functionality of anthranil was exploited, wherein the nitrogen has been used...

Cited by 21 publications

References 62 publications

Transition Metal‐Mediated Functionalization of Isoxazoles: A Review

Transition Metal‐Mediated Functionalization of Isoxazoles: A Review

Synthesis of acridinesviacopper-catalyzed amination/annulation cascades between arylboronic acids and anthranils

Data-Driven Analysis of Reactions Catalyzed by [CoCp*(CO)I₂]

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Cp*Co(iii)-catalyzed C–H amination/annulation cascade of sulfoxonium ylides with anthranils for the synthesis of indoloindolones

Abstract: Cp*Co(III)-catalyzed [4+1] annulation of sulfoxonium ylides with anthranils has been developed for the synthesis of indole-indolone scaffolds. The dual functionality of anthranil was exploited, wherein the nitrogen has been used...

Cited by 21 publications

References 62 publications

Transition Metal‐Mediated Functionalization of Isoxazoles: A Review

Transition Metal‐Mediated Functionalization of Isoxazoles: A Review

Synthesis of acridinesviacopper-catalyzed amination/annulation cascades between arylboronic acids and anthranils

Data-Driven Analysis of Reactions Catalyzed by [CoCp*(CO)I2]

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Data-Driven Analysis of Reactions Catalyzed by [CoCp*(CO)I₂]