Redox-Neutral Couplings between Amides and Alkynes via Cobalt(III)-Catalyzed C–H Activation

Kong, Lingheng; Yu, Songjie; Zhou, Xukai; Li, Xingwei

doi:10.1021/acs.orglett.5b03629

Cited by 144 publications

(38 citation statements)

References 69 publications

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“…181,182 Li published the first method in this area with the Co(III)-catalyzed synthesis of quinolines 331 from anilides 330 and alkyne coupling partners (Scheme 149). 181 Here the Co(III)-intermediate formed upon addition of the alkyne presumably cyclizes upon the amide carbonyl to generate a hemiaminal intermediate, which then undergoes aromatization with loss of water to generate quinoline 331 . While catalytic amounts of the silver additive were found to facilitate the reaction, stoichiometric quantities provided the highest yields.…”

Section: Additions To C=c π-Bonds Followed By Cyclization Upon Pomentioning

confidence: 99%

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

2016

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The transition metal-catalyzed addition of C–H bonds to carbonyls, imines and related polarized π-bonds has emerged as a particularly efficient and powerful approach for the construction of an incredibly diverse array of heteroatom substituted products. Readily available and stable inputs are typically employed, and reactions often proceed with very high functionality group compatibility and without the production of waste byproducts. Additionally, many transition metal-catalyzed C–H bond additions to polarized π-bonds occur within cascade reaction sequences to provide rapid access to a diverse array of different heterocyclic as well as carbocyclic products. This review highlights the diversity of transformations that have been achieved, catalysts that have been used, and types of products that have been prepared through the transition metal catalyzed addition of C–H bonds to carbonyls, imines and related polarized π-bonds.

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Section: Additions To C=c π-Bonds Followed By Cyclization Upon Pomentioning

confidence: 99%

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

2016

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“…We therefore sought to utilize 3 ket ‐I , 3 CONHtBu ‐I , and 3 acetanilide ‐I as a platform for determining the intermediacy of these species in representative catalytic reactions. Importantly, these directing groups have been utilized in Cp*Co‐catalyzed C−H functionalization reactions . As shown in Figure , these cyclometalated complexes proved to be suitable catalysts for representative C−C coupling reactions, thus supporting the feasibility of the corresponding cationic intermediates in these transformations…”

Section: Figurementioning

confidence: 74%

Weakly Coordinated Cobaltacycles: Trapping Catalytically Competent Intermediates in Cp*Co^IIICatalysis

et al. 2020

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Herein, we disclose the synthesis of metallacyclic Cp*CoIII complexes containing weakly chelating functional groups. We have employed these compounds not only as an exceptional platform for accessing some of the most widely invoked transient intermediates in C−H functionalization processes but also as competent catalysts in different Cp*Co‐catalyzed transformations, including a benchmark coupling reaction.

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“…The Li group reported redox‐annulative coupling reactions catalyzed by Co(III) with NH amide as the directing group (Scheme ) . Traditional synthetic methods for quinolines usually encounter various strict restrictions, such as the use of corrosive reagents and toxic reagents as well as the limited substrate scope.…”

Section: Ortho‐c–h Functionalization Of Aromatic Amidesmentioning

confidence: 99%

C–H Functionalization of Aromatic Amides

et al. 2020

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Since the beginning of the 21st century, significant progress has been made in transition metal‐catalyzed C–H functionalization of aromatic amides. The achievements in this field have mainly focused on ortho (proximal) functionalization, there have been far fewer reports on remote C–H functionalization, and para‐ and meta‐selective functionalizations remain a major challenge. Interestingly, there are few related comments in this field. In a few published cases, the scope of the report is relatively narrow, either to comment on the functionalization of a specific directing group or to summarize the functionalization of a specific reaction site. Herein, for the first time, we have comprehensively summarized the C–H functionalization of aromatic amides. This review is divided into three parts: ortho‐, para‐ and meta‐C–H functionalization of aromatic amides, and is subdivided according to the type of catalyst. The directing groups, reaction types, conditions, mechanism and applications of the corresponding reactions are discussed in detail.

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Redox-Neutral Couplings between Amides and Alkynes via Cobalt(III)-Catalyzed C–H Activation

Cited by 144 publications

References 69 publications

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

Weakly Coordinated Cobaltacycles: Trapping Catalytically Competent Intermediates in Cp*Co^IIICatalysis

C–H Functionalization of Aromatic Amides

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Redox-Neutral Couplings between Amides and Alkynes via Cobalt(III)-Catalyzed C–H Activation

Cited by 144 publications

References 69 publications

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

Weakly Coordinated Cobaltacycles: Trapping Catalytically Competent Intermediates in Cp*CoIIICatalysis

C–H Functionalization of Aromatic Amides

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Weakly Coordinated Cobaltacycles: Trapping Catalytically Competent Intermediates in Cp*Co^IIICatalysis