Recent advances in decarbonylative annulation reactions

Saikia, Pallabi; Gogoi, Sanjib

doi:10.1039/d1ob00891a

Cited by 8 publications

(1 citation statement)

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“…[74] Albeit, annulation reactions hold a special place in synthetic organic chemistry as they construct molecular complexity in single step and applicable in drug development. [75] In this context, there is need for new technologies for conducting chemical transformations. Recent progress in the development of MN(SiMe 3 ) 2 mediated transformations in the synthesis of biologically important heterocycles has surged, and attracts chemists from both industry and academia.…”

Section: Annulationmentioning

confidence: 99%

Masters of Mediation: MN(SiMe₃)₂ in Functionalization of C(sp³)−H Latent Nucleophiles

Sreedharan,

Gandhi

2024

Chemistry A European J

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Organoalkali compounds have undergone a far‐reaching transformation being a coupling partner to a mediator in unusual organic conversions which finds its spot in the field of sustainable synthesis. Transition‐metal catalysis has always been the priority in C(sp3)−H bond functionalization, however alternatively, in recent times this has been seriously challenged by earth‐abundant alkali metals and their complexes arriving at new sustainable organometallic reagents. In this line, the importance of MN(SiMe3)2 (M = Li, Na, K & Cs) reagent revived in C(sp3)−H bond functionalization over recent years in organic synthesis is showcased in this minireview. MN(SiMe3)2 reagent with higher reactivity, enhanced stability, and bespoke cation‐π interaction have shown eye‐opening mediated processes such as C(sp3)−C(sp3) cross‐coupling, radical‐radical cross‐coupling, aminobenzylation, annulation, aroylation, and other transformations to utilize readily available petrochemical feedstocks. This article also emphasizes the unusual reactivity of MN(SiMe3)2 reagent in unreactive and robust C−X (X = O, N, F, C) bond cleavage reactions that occurred alongside the C(sp3)−H bond functionalization. Overall, this review encourages the community to exploit the untapped potential of MN(SiMe3)2 reagent and also inspires them to take up this subject to even greater heights.

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Section: Annulationmentioning

confidence: 99%

Masters of Mediation: MN(SiMe₃)₂ in Functionalization of C(sp³)−H Latent Nucleophiles

Sreedharan,

Gandhi

2024

Chemistry A European J

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Exploring the Divergent Reactivity of Vinyl Radicals Emanating from Alkynes and Thiols via Photoredox Catalysis

Kumar,

Ali Shah

2023

Chemistry An Asian Journal

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Organic chemistry has seen a surge in visible‐light‐driven transformations, which offer unique reaction pathways and access to new synthetic possibilities. We aim to provide a comprehensive understanding of state‐of‐the‐art photo‐mediated alkyne functionalization, with a focus on the reactive behavior of vinyl radicals. This review outlines our contributions to the field, including developing new methods for forming carbon‐carbon and carbon‐heteroatom bonds.

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Cationic Iridium‐Catalyzed Asymmetric Decarbonylative Aryl Addition of Aromatic Aldehydes to Bicyclic Alkenes

Nonami

Morimoto

Kanemoto

et al. 2022

Chemistry A European J

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We report an unprecedented catalytic protocol for the enantioselective decarbonylative transformation of aryl aldehydes. In this process, the decarbonylation of aldehydes catalyzed by chiral iridium complexes enabled the formation of asymmetric CÀ C bonds through the formation of an arylÀ iridium intermediate. The decarbonylative aryl addition to bicyclic alkenes was fluidly performed without a stoichio-metric arylÀ metal reagent, such as aryl boronic acid, with a cationic iridium complex generated in situ from Ir(cod) 2 (BAr F 4 ) and the sulfur-linked bis(phosphoramidite) ligand ((R,R)-SÀ MeÀ BIPAM). This reaction has broad functional group compatibility, and no waste is generated, except carbon monoxide.

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Recent advances in decarbonylative annulation reactions

Abstract: In recent years the decarbonylative annulation reactions have emerged as one of the most efficient routes to construct variety of important carbocyclic and heterocyclic scaffolds. The main advantages of this...

Cited by 8 publications

References 91 publications

Masters of Mediation: MN(SiMe₃)₂ in Functionalization of C(sp³)−H Latent Nucleophiles

Masters of Mediation: MN(SiMe₃)₂ in Functionalization of C(sp³)−H Latent Nucleophiles

Exploring the Divergent Reactivity of Vinyl Radicals Emanating from Alkynes and Thiols via Photoredox Catalysis

Cationic Iridium‐Catalyzed Asymmetric Decarbonylative Aryl Addition of Aromatic Aldehydes to Bicyclic Alkenes

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Recent advances in decarbonylative annulation reactions

Abstract: In recent years the decarbonylative annulation reactions have emerged as one of the most efficient routes to construct variety of important carbocyclic and heterocyclic scaffolds. The main advantages of this...

Cited by 8 publications

References 91 publications

Masters of Mediation: MN(SiMe3)2 in Functionalization of C(sp3)−H Latent Nucleophiles

Masters of Mediation: MN(SiMe3)2 in Functionalization of C(sp3)−H Latent Nucleophiles

Exploring the Divergent Reactivity of Vinyl Radicals Emanating from Alkynes and Thiols via Photoredox Catalysis

Cationic Iridium‐Catalyzed Asymmetric Decarbonylative Aryl Addition of Aromatic Aldehydes to Bicyclic Alkenes

Contact Info

Product

Resources

About

Masters of Mediation: MN(SiMe₃)₂ in Functionalization of C(sp³)−H Latent Nucleophiles

Masters of Mediation: MN(SiMe₃)₂ in Functionalization of C(sp³)−H Latent Nucleophiles