Rapid Nickel-Catalyzed Suzuki−Miyaura Cross-Couplings of Aryl Carbamates and Sulfamates Utilizing Microwave Heating

Baghbanzadeh, Mostafa; Pilger, Christian; Kappe, C. Oliver

doi:10.1021/jo1024464

Cited by 129 publications

(69 citation statements)

References 42 publications

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“…Of the phase transfer catalysts studied, polyethylene glycol 200 (PEG-200) was found to be a good choice probably because it avoids the acyl chloride hydrolysis issue as well as promoting better base solubilization. The replacement of traditionally used Pd with less expensive Ni-based catalyst systems was approached by Kappe et al in 2011 [81]. The Ni-catalyzed SMC reactions were performed using aryl carbamates and/or sulfamates as the electrophilic coupling partners for reactions, because they are readily available and more stable under a variety of reaction conditions than the more reactive triflates.…”

Section: Moving From Homogeneous To Heterogeneous Catalysis In Mw Promentioning

confidence: 99%

Eco-Friendly Physical Activation Methods for Suzuki–Miyaura Reactions

et al. 2017

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Eco-compatible activation methods in Suzuki-Miyaura cross-coupling reactions offer challenging opportunities for the design of clean and efficient synthetic processes. The main enabling technologies described in the literature are microwaves, ultrasound, grinding (mechanochemistry) and light. These methods can be performed in water or other green solvents with phase-transfer catalysis or even in solventless conditions. In this review, the authors will summarize the progress in this field mainly from 2010 up to the present day.

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Section: Moving From Homogeneous To Heterogeneous Catalysis In Mw Promentioning

confidence: 99%

Eco-Friendly Physical Activation Methods for Suzuki–Miyaura Reactions

et al. 2017

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“…Other examples can also be found, where MW irradiation proved to be beneficial in Suzuki-Miyaura cross-couplings by shortening the reaction times (usually to minutes), and increasing the yields, as compared to those obtained by traditional heating [8,[11][12][13].…”

Section: Suzuki-miyaura Reactionmentioning

confidence: 99%

Microwave-Assisted Syntheses in Organic Chemistry

Kiss

Bálint²,

Keglevich

2016

SpringerBriefs in Molecular Science

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The second part focuses on the summary of typical organic chemical reactions selected, such as coupling reactions (C-C bond formation reactions, carbon-heteroatom bond formations), condensations (aldol-type-, Claisen-, Knoevenagel reaction), multicomponent reactions (Mannich-, Biginelli-, Hantzsch-, Bucherer-Bergs-, Strecker-, Gewald-, Kabachnik-Fields-, Kindler-, Passerini-, Ugi-and domino reactions), cycloadditions (including Diels-Alder reactions). The authors tried to compile fashionable reactions that have been reviewed less in the past years.

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“…Van der Eycken and co-workers employed a microwave-assisted Suzuki-Miyaura cross-coupling reaction in a synthetic route to aza analogs of (−)steganacin [71]. A number of electron-rich aryl bromides were effectively coupled with o-formylphenylboronic acids to produce an array of sterically congested biaryls after only 15 In 2011, Kappe and co-workers reported the Ni-catalyzed Suzuki-Miyaura cross-coupling of arylboronic acids and aryl carbamates and sulfamates utilizing microwave heating [72]. Good to excellent yields of the biaryl products were obtained using various coupling partners (Scheme 15.20).…”

Section: Cross-coupling Reactions 615mentioning

confidence: 99%