Cobalt-Catalyzed Oxidant-Free Spirocycle Synthesis by Liberation of Hydrogen

Lv, Ningning; Liu, Yue; Xiong, Chunhua; Liu, Zhanxiang; Zhang, Yuhong

doi:10.1021/acs.orglett.7b02266

Cited by 112 publications

(45 citation statements)

References 73 publications

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“…Benzimidate, as a powerful traceless directing group, [6] has been frequently used for the synthesis of structurally diverse heterocycles through reacting with diverse coupling partners, [6] especially with different kinds of alkenes. [7] In 2016, Liu and co-workers demonstrated that ruthenium-catalyzed annulation of benzimidates and acrylates can construct the lactam derivatives (Scheme 1a). [7a] Later, Ackermann and coworkers reported the cascade CÀ H/NÀ H allylation of aryl imidates in the presence of low-cost cobalt(III) catalyst (Scheme 1b).…”

mentioning

confidence: 99%

Rhodium‐Catalyzed Cascade Annulation of Benzimidates and Nitroalkenes for the Synthesis of Difunctionalized Indenes

Chen

Liu

et al. 2019

Adv Synth Catal

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A facile and expeditious protocol for the synthesis of difunctionalized indenes from readily available benzimidates and nitroalkenes through rhodium-catalyzed CÀ H activation and cyclization is reported here. The transformation exhibits powerful reactivity, tolerates a large number of functional groups, and proceeds in moderate to high yields under an ambient atmosphere, providing a straightforward method to access structurally diverse and valuable difunctionalized indene derivatives.

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mentioning

confidence: 99%

Rhodium‐Catalyzed Cascade Annulation of Benzimidates and Nitroalkenes for the Synthesis of Difunctionalized Indenes

Chen

Liu

et al. 2019

Adv Synth Catal

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“…(1)].T he quinones played ad ual role as both one carbon component for the annulation and oxidant. Very recently,acobalt-catalyzed [4+ +1] cyclization of benzimidates with maleimides was also reported by Zhang et al [123] [Scheme 77, Eq. (2)].I ntriguingly,t his transformation occursi nt he absence of oxidantw ith the liberation of hydrogen instead.…”

Section: With Alkenes or Allenesmentioning

confidence: 88%

Transition‐Metal‐Catalyzed C−H Functionalization for Construction of Quaternary Carbon Centers

2018

Chemistry A European J

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Efficient construction of quaternary carbon centers represents one of the most challenging goals in organic synthesis, and it has drawn tremendous research interest from organic chemist community. The past decade has witnessed a significant advancement of direct C-H functionalization, which delivers various synthetic tools for assembling structurally diversified architectures with the advantage of step- and atom-economy, operational simplicity, and readily available substrates. In this Minireview, synthetic methods based on transition-metal-catalyzed C-H functionalization as efficient tools for the construction of quaternary carbon centers are summarized.

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“…In 2018, Zhang and his co‐workers have reported the synthesis of spirosuccinimide derivatives from benzimidates with maleimides in the presence of Cp*Co(CO)I 2 without having any auxiliary ligand . This methodology furnished spirosuccinimides in good to excellent yields without any silver oxidant and also liberates H 2 gas as a side product.…”

Section: Annulation Of Aromatics With Maleimidesmentioning

confidence: 99%

Alkylation, Annulation, and Alkenylation of Organic Molecules with Maleimides by Transition‐Metal‐Catalyzed C‐H Bond Activation

2019

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Maleimide and succinimide core moieties are present in various natural products and pharmaceuticals. In addition, these derivatives can be readily modified into biologically important organic molecules including pyrrolidines and γ-lactams. A transition-metal-catalyzed chelationassisted functionalization of inert CÀ H bond of organic molecules with electrophiles or nucleophiles is one of the efficient methods to construct chemical bonds in a highly atom-and step-economical manner. The present review describes the recent advances in the reaction involving maleimides with organic molecules by a chelation-assisted inert CÀ H bond activation methodology. The reaction involving maleimides with organic molecules having directing groups, such as ketone, acyl, pyridyl, pyrimidyl, oxime, amide, imidate, chromone, azo, N-sulfonyl ketimine, carboxylic acids, and aldimines, were described. The scope, limitation and mechanistic investigation of the alkylation, annulation and alkenylation reactions were discussed elaborately. This review article includes the entire report on the chemical bondforming reaction of maleimides with organic molecules by the CÀ H bond activation strategy until the end of 2018.

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Cobalt-Catalyzed Oxidant-Free Spirocycle Synthesis by Liberation of Hydrogen

Cited by 112 publications

References 73 publications

Rhodium‐Catalyzed Cascade Annulation of Benzimidates and Nitroalkenes for the Synthesis of Difunctionalized Indenes

Rhodium‐Catalyzed Cascade Annulation of Benzimidates and Nitroalkenes for the Synthesis of Difunctionalized Indenes

Transition‐Metal‐Catalyzed C−H Functionalization for Construction of Quaternary Carbon Centers

Alkylation, Annulation, and Alkenylation of Organic Molecules with Maleimides by Transition‐Metal‐Catalyzed C‐H Bond Activation

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