Ruthenium-Catalyzed Cross-Coupling of Maleimides with Alkenes

Morita, Toshiteru; Akita, M.; Satoh, Tetsuya; Kakiuchi, Fumitoshi; Miura, Masahiro

doi:10.1021/acs.orglett.6b02244

Cited by 29 publications

(16 citation statements)

References 58 publications

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“…The reaction of maleimides 2 a with alkenes 2 b – c in presence of Rh/Ru‐salts afforded corresponding 3‐substituted itaconimides 1 in good yield (Scheme 2). [17,18] The reaction has a broad scope with excellent functional group tolerance with respect to alkenes. The proposed mechanism involved directing group‐assisted vinyl C−H activation to generate rhodacycle 2 d , which on carbometallation with itaconimides led to the formation of rhodacycle 2 e .…”

Section: Synthetic Approaches For Itaconimide Derivativesmentioning

confidence: 99%

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A Review on the Synthesis and Applications of α‐Alkylidene Succinimides

Nagaraju

Nanda

2022

Asian J Org Chem

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The widespread biological activity and manifestation of multiple reactive centers in itaconimides/α‐alkylidene succinimides have made them as one of the valuable synthetic targets. In this domain, various strategies have been developed to portray the proficiency of these N‐bearing heterocycles. The current review summarizes the biological activity, synthesis, and use of itaconimides/α‐alkylidene succinimide in numerous useful transformations under many reacting environments.

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Section: Synthetic Approaches For Itaconimide Derivativesmentioning

confidence: 99%

“…The reaction of maleimides 2 a with alkenes 2 b-c in presence of Rh/Ru-salts afforded corresponding 3-substituted itaconimides 1 in good yield (Scheme 2). [17,18] The reaction has a broad scope with excellent functional group tolerance with respect to alkenes. The proposed mechanism involved directing…”

Section: Synthetic Approaches For Itaconimide Derivativesmentioning

confidence: 99%

A Review on the Synthesis and Applications of α‐Alkylidene Succinimides

Nagaraju

Nanda

2022

Asian J Org Chem

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“…Codimerization of alkenes is a promising, atom-efficient synthetic method that affords highly substituted alkenes with various functionalities from simple alkenes. − Thus far, Co, − Ni, − ,,− Ru, − Rh, ,,, Pd, − other transition-metal − complexes, and Lewis or Brønsted acids − have been used as catalysts for this r...…”

Section: Introductionmentioning

confidence: 99%

Ruthenacyclopentanes as Intermediates in the Regio- and Stereoselective Linear Codimerization ofN-Vinylamides with Electron-Deficient Alkenes

et al. 2017

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Tricarbonylruthenacyclopentanes were successfully synthesized by in situ reduction of RuCl3 with Zn-Cu/CO in the presence of N-vinylacetamides and electron-deficient alkenes such as ethyl acrylate, dimethyl fumarate, and dimethyl maleate. X-ray crystallography of the ruthenacyclopentanes revealed that the three carbonyl ligands occupied coordination sites facially, and the ruthenacycle moiety was stabilized by coordination with the acetamido oxygen atom. When the ruthenacyclopentanes in toluene or DMA were heated to 130 °C for 24 h, linear codimers of the alkenes were formed in moderate to good yield. Both the ruthenacyclopentane and the RuCl3/Zn-Cu/alcohol system showed catalytic activity for the linear codimerization of alkenes, affording the codimers in good yield. The results of stoichiometric and catalytic reactions revealed that the codimerization can proceed via ruthenacyclopentane intermediates.

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“…Recently, Ackermann and Li et al disclosed cobalt(III) catalysis for C–H alkylation of arenes with maleimides, where substrates were modified through the installation of a strongly coordinating pyrimidine unit as a directing group . Apart from these selective accomplishments, hydroarylation of maleimides through a C–H bond activation strategy that maximizes step and atom economy remains unsatisfied and urges immediate attention …”

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confidence: 99%

Ruthenium(II)-Catalyzed Hydroarylation of Maleimides Using Carboxylic Acids as a Traceless Directing Group

et al. 2017

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An efficient Ru(II)-catalyzed hydroarylation of maleimides with ready-stock aryl carboxylic acids has been developed based on weak carboxylate-directed ortho-C-H alkylation and concomitant decarboxylation processes, fabricating 3-aryl succinimides, a recurrent scaffold in drug molecules, in high yields (up to 97%). The protocol features operational simplicity, avoids the need for precious metal additives/oxidants, and offers broad substrate scope with formal meta- and para-selectivities. It represents the first example of Ru(II)-catalyzed direct arylation of maleimides with unbiased benzoic acids.

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Ruthenium-Catalyzed Cross-Coupling of Maleimides with Alkenes

Abstract: The cross-coupling of maleimides with electron-deficient alkenes such as acrylates proceeds smoothly under ruthenium catalysis. This unique C-C coupling provides a simple, straightforward synthetic method for preparing alkylidene succinimide derivatives.

Cited by 29 publications

References 58 publications

A Review on the Synthesis and Applications of α‐Alkylidene Succinimides

A Review on the Synthesis and Applications of α‐Alkylidene Succinimides

Ruthenacyclopentanes as Intermediates in the Regio- and Stereoselective Linear Codimerization ofN-Vinylamides with Electron-Deficient Alkenes

Ruthenium(II)-Catalyzed Hydroarylation of Maleimides Using Carboxylic Acids as a Traceless Directing Group

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