Synthesis of Multiply Substituted Polycyclic Aromatic Hydrocarbons by Iridium‐Catalyzed Annulation of Ring‐Fused Benzocyclobutenol with Alkyne through C−C Bond Cleavage

Yu, Jiajia; Yan, Hong; Zhu, Chen

doi:10.1002/ange.201509973

Cited by 16 publications

(2 citation statements)

References 53 publications

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“…Further, the proposed catalytic cycle has been depicted in scheme 41, where the reaction was initiated with the generation of active Ir-catalyst A, from the Ir-dimer complex. Then 53 Where the metal coordinates through free -OH for the insertion between C-C bond to generate the M-C bond. The authors examined the scope of the reaction, which revealed the general trend in the reactivities of the substrates and alkynes.…”

Section: Various Transition Metal-catalyzed Unusual Reactions Of Alkynementioning

confidence: 99%

Reactivity of Alkynes with M-C Bonds generated through C-H Activation

Banjare

Mahulkar

Nanda

et al. 2022

Preprint

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Transition metal-catalyzed C-H activation and functionalization with various coupling partners is a well-explored area of research. Among the various coupling partners used, alkynes occupy a prominent position on account of their varied reactivity. Due to their low steric demand and a high degree of unsaturation they effectively overlap with metal d-orbitals and form multiple bond-forming events giving rise to complex skeletons that are otherwise challenging to synthesize. This makes alkyne one of the most successful coupling partners in terms of the number of useful transformations. Remarkably, by changing the reaction conditions and transition-metals from 5d to 3d, the behaviors of alkynes also change. Despite enormous explorations with alkynes, there are still a lot more possible ways by which alkynes can be made to react with M-C bonds generated through C-H activation. Especially with the development of new high and low valent first-row metal catalysts, there is plenty of scope for this chemistry to evolve as one of the most explored areas of research in coming years. Therefore, a review on this topic is both timely and useful for synthetic chemists who are working in this area. In this review, we have highlighted the diverse reactivity of alkynes with various transition metals and their applications along with some of our thoughts on future prospects.

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Section: Various Transition Metal-catalyzed Unusual Reactions Of Alkynementioning

confidence: 99%

Reactivity of Alkynes with M-C Bonds generated through C-H Activation

Banjare

Mahulkar

Nanda

et al. 2022

Preprint

View full text Add to dashboard Cite

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“…In comparison, owing to a surrounding environment composed of four bonding atoms, regioselective alkyl deconstructive carbofunctionalization has at present remained a challenging but highly valuable topic in synthetic chemistry, as this process would offer the potential to develop novel transformations producing functional molecules that are difficult to prepare or inaccessible by conventional approaches (Liu et al., 2018). For instance in this regard, the Zhu group has reported a number of transformations on the cleavage of strained alkyl chains such as cyclobutanols (Ren et al., 2015, Ren et al., 2016, Yu et al., 2016, Zhao et al., 2015). Very recently, Roque et al.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Multisubstituted Benzimidazolones via Copper-Catalyzed Oxidative Tandem C–H Aminations and Alkyl Deconstructive Carbofunctionalization

et al. 2019

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Summary Benzimidazolone constitutes the core structure of numerous pharmaceuticals, agrochemicals, inhibitors, pigments, herbicides, and fine chemicals. Amination of hydrocarbons is an attractive tool for the creation of nitrogen-containing products. However, the multiple steps, harsh conditions, and low atom efficiencies often present in these reactions remain challenging. We present a multicomponent synthesis of functional benzimidazolones from arylamines, dialkylamines, and alcohols, acting via the sequence of copper-catalyzed oxidative tandem C–H aminations and alkyl deconstructive carbofunctionalization. The catalytic transformation forms multiple bonds in one single operation, uses readily available feedstocks and a naturally abundant Cu/O 2 catalyst system, has broad substrate scope, avoids pre-installation of aminating agents and directing groups, and provides high chemo- and regioselectivity, resulting in direct functionalization of inert C–H and C–C bonds via single-electron oxidation-induced activation mode. This platform can be expected to provide structurally diverse products with interesting biological, chemical, and physical properties.

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Palladium‐Catalyzed Ring‐Opening of 2‐Alkylidenecyclobutanols: Stereoselective Synthesis of γ,δ‐Unsaturated Ketones by C−C Bond Cleavage

Chen

Sun

et al. 2017

Adv Synth Catal

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A facile synthesis of g,d-unsaturated ketones via palladium-catalyzed ring-opening of 2alkylidenecyclobutanols with organic halides is described. The key step involves C sp 3ÀC sp 2 bond cleavage via palladium-catalyzed b-carbon elimination. The desired g,d-unsaturated ketones are obtained in good to excellent yields and broad functional group tolerability. Aryl, heteroaryl, benzyl, and alkynyl halides all readily participate to forge tri-substituted carbon-carbon double bond in a stereoselective manner.

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Synthesis of Multiply Substituted Polycyclic Aromatic Hydrocarbons by Iridium‐Catalyzed Annulation of Ring‐Fused Benzocyclobutenol with Alkyne through C−C Bond Cleavage

Cited by 16 publications

References 53 publications

Reactivity of Alkynes with M-C Bonds generated through C-H Activation

Reactivity of Alkynes with M-C Bonds generated through C-H Activation

Synthesis of Multisubstituted Benzimidazolones via Copper-Catalyzed Oxidative Tandem C–H Aminations and Alkyl Deconstructive Carbofunctionalization

Palladium‐Catalyzed Ring‐Opening of 2‐Alkylidenecyclobutanols: Stereoselective Synthesis of γ,δ‐Unsaturated Ketones by C−C Bond Cleavage

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