Transition-Metal-Catalyzed Oxidative Heck Reactions

Karimi, Babak; Behzadnia, Hesam; Elhamifar, Dawood; Akhavan, Pari Fadavi; Esfahani, Farhad Kabiri; Zamani, Asghar

doi:10.1055/s-0029-1218748

Cited by 207 publications

(67 citation statements)

References 86 publications

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“…Karimi et al [39] have reviewed similar types of reactions describing the oxidative Heck reactions of organometallic compounds such as organomercuric acetates, organoboronic acids, organofluorosilicates and arylstannanes. A number of successful examples are given for the intermolecular, intramolecular, nonsymmetrical, asymmetrical oxidative Heck reaction in presence or in absence of air, with ligand-free or ligand based catalysts formed from palladium, polymer supported palladium(II), transition metal and organometallic catalysts other than palladium along with the examples of asymmetric reactions, intermolecular and intramolecular oxidative Heck reactions via C-H activation.…”

Section: Dehydrogenative/oxidative Heck Reactionmentioning

confidence: 99%

Heck Reaction—State of the Art

Jagtap¹

2017

Catalysts

181

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Abstract:The Heck reaction is one of the most studied coupling reactions and is recognized with the Nobel Prize in Chemistry. Thousands of articles, hundreds of reviews and a number of books have been published on this topic. All reviews are written exhaustively describing the various aspects of Heck reaction and refer to the work done hitherto. Looking at the quantum of the monographs published, and the reviews based on them, we found a necessity to summarize all reviews on Heck reaction about catalysts, ligands, suggested mechanisms, conditions, methodologies and the compounds formed via Heck reaction in one review and generate a resource of information. One can find almost all the catalysts used so far for Heck reaction in this review.

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Section: Dehydrogenative/oxidative Heck Reactionmentioning

confidence: 99%

Heck Reaction—State of the Art

Jagtap¹

2017

Catalysts

181

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“…Furthermore, the oxidative Heck cross-coupling reactions have become attractive for modern organic synthesis due to advantages such as efficiency, mild reaction conditions, good functional group tolerance, and widespread applications [62][63][64]. In 2017, Arvidsson and co-workers reported an operationally simple method for ligand-and additive-free oxidative Heck couplings of aryl boronic acids (57) with ESF (51) (Scheme 10) [65].…”

Section: Fluorine-containing Vinyl Sulfur Compounds As the Cross-coupmentioning

confidence: 99%

“…A plausible reaction mechanism was suggested in Scheme 21 [78]. The reaction presumably proceeded via (1) oxidative addition of aryldiazonium salt (106) to Pd(0), leading to an arylpalladium complex (110), (2) Arylboronic acids are an important class of compounds for coupling reactions, which are stable in air and to moisture, and they are compatible with a broad range of common functional groups [62][63][64]. In 2015, Lu and co-workers presented the first oxidative Heck-type reactions of arylboronic acids with fluoroalkylated olefin [79].…”

Section: Scheme 17 Preparation Of Diazonium-functionalized Oligo(phementioning

confidence: 99%

“…Arylboronic acids are an important class of compounds for coupling reactions, which are stable in air and to moisture, and they are compatible with a broad range of common functional groups [62][63][64]. In 2015, Lu and co-workers presented the first oxidative Heck-type reactions of arylboronic acids with fluoroalkylated olefin [79].…”

Section: Scheme 17 Preparation Of Diazonium-functionalized Oligo(phementioning

confidence: 99%

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Pd-Catalyzed Mizoroki-Heck Reactions Using Fluorine-Containing Agents as the Cross-Coupling Partners

Yang

Zhao

et al. 2018

Catalysts

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Abstract:The Mizoroki-Heck reaction represents one of the most convenient methods for carbon-carbon double bond formation in the synthesis of small organic molecules, natural products, pharmaceuticals, agrochemicals, and functional materials. Fluorine-containing organic compounds have found wide applications in the research areas of materials and life sciences over the past several decades. The incorporation of fluorine-containing segments into the target molecules by the Mizoroki-Heck reactions is highly attractive, as these reactions efficiently construct carbon-carbon double bonds bearing fluorinated functional groups by simple procedures. This review summarizes the palladium-catalyzed Mizoroki-Heck reactions using various fluorine-containing reagents as the cross-coupling partners. The first part of the review describes the Pd-catalyzed Mizoroki-Heck reactions of aryl halides or pseudo-halides with the fluorinated alkenes, and the second part discusses the Pd-catalyzed Mizoroki-Heck reactions of the fluorinated halides or pseudo-halides with alkenes. Variants of the Pd-catalyzed Mizoroki-Heck reactions with fluorine-containing reagents are also briefly depicted. This work supplies an overview, as well as a guide, to both younger and more established researchers in order to attract more attention and contributions in the realm of Mizoroki-Heck reactions with fluorine-containing participants.

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“…This avoids the formation of stoichiometric amounts of the corresponding salts which typically cause extensive environmental pollution [121,122]. From a mechanistic point of view, these transformations involve catalytic amounts of a Pd(II) species which initially undergoes an oxidative addition of the nucleophile followed by coordination of an alkene, β-hydride elimination, and reductive elimination of the desired product.…”

Section: Oxidative Carbon-carbon Coupling Reactionsmentioning

confidence: 99%

Aerobic Oxidations in Continuous Flow

Pieber

Kappe

2015

Organometallic Flow Chemistry

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In recent years, the high demand for sustainable processes resulted in the development of highly attractive oxidation protocols utilizing molecular oxygen or even air instead of more uneconomic and often toxic reagents. The application of these sustainable, gaseous oxidants in conventional batch reactors is often associated with severe safety risks and process challenges especially on larger scales. Continuous flow technology offers the possibility to minimize these safety hazards and concurrently allows working in high-temperature/high-pressure regimes to access highly efficient oxidation protocols. This review article critically discusses recent literature examples of flow methodologies for selective aerobic oxidations of organic compounds. Several technologies and reactor designs for biphasic gas/liquid as well as supercritical reaction media are presented in detail.

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Transition-Metal-Catalyzed Oxidative Heck Reactions

Cited by 207 publications

References 86 publications

Heck Reaction—State of the Art

Heck Reaction—State of the Art

Pd-Catalyzed Mizoroki-Heck Reactions Using Fluorine-Containing Agents as the Cross-Coupling Partners

Aerobic Oxidations in Continuous Flow

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