Non-noble metal-catalysed carbonylative transformations

Li, Yahui; Hu, Yuya; Wu, Xiao‐Feng

doi:10.1039/c7cs00529f

Cited by 225 publications

(66 citation statements)

References 178 publications

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“…Metal Content in the Earth's crust [ppm] [9] Price [E/mol] [10] IV This shift poses new challenges and introduces novel catalytic mechanisms of action that offer exciting opportunities for further reaction development. [11] With this Minire-view,w ew ould like to focus the attention of the synthetic organic chemist to promising base metal catalyzed processes involving isocyanide insertion and highlight proposed mechanistic aspects of these interesting reactions.…”

Section: Groupmentioning

confidence: 99%

Base Metal Catalyzed Isocyanide Insertions

et al. 2019

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Isocyanides are diverse C1 building blocks considering their potential to react with nucleophiles, electrophiles, and radicals. Therefore, perhaps not surprisingly, isocyanides are highly valuable as inputs for multicomponent reactions (MCRs) and other one‐pot cascade processes. In the field of organometallic chemistry, isocyanides typically serve as ligands for transition metals. The coordination of isocyanides to metal centers alters the electronic distribution of the isocyano moiety, and reaction pathways can therefore be accessed that are not possible in the absence of the metal. The tunable reactivity of the isocyanide functional group by transition metals has evolved into numerous useful applications. Especially palladium‐catalyzed isocyanide insertion processes have emerged as powerful reactions in the past decade. However, reports on the use of earth‐abundant and cheap base metals in these types of transformations are scarce and have received far less attention. In this Minireview, we focus on these emerging base metal catalyzed reactions and highlight their potential in synthetic organic chemistry. Although mechanistic studies are still scarce, we discuss distinct proposed catalytic cycles and categorize the literature according to 1) the (hetero)atom bound to and 2) the type of bonding with the transition metal in which the (formal) insertion occurs.

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Section: Groupmentioning

confidence: 99%

Base Metal Catalyzed Isocyanide Insertions

et al. 2019

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“…Although homogeneous palladium complexes have been demonstrated to be quite successful in many carbonylation reactions, while they still suffer from some drawbacks including: (i) contamination of the final products by the palladium and ligand residues; (ii) problems of separation and reuse of the catalyst; and (iii) destruction of palladium complex during the catalytic reaction. Heterogeneous switching of a homogeneous palladium complex by immobilizing the complex onto a solid support with a covalent bond has been expected to address these problems, where traditional polymers and silicas are the most widely used support materials .…”

Section: Introductionmentioning

confidence: 99%

Carbonylative Suzuki coupling and alkoxycarbonylation of aryl halides using palladium supported on phosphorus‐doped porous organic polymer as an active and robust catalyst

Wan

Song

et al. 2018

Applied Organom Chemis

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Developing highly active catalysts with the combined advantages of molecular and solid catalysis is considered as the “Holy Grail” in the area of catalysis research. Herein, a phosphorus‐doped porous polymer‐immobilized palladium was successfully developed as an efficient, robust, and recyclable catalyst for the carbonylative Suzuki coupling and alkoxycarbonylation reactions of aryl halides. Rather than just as an immobilizing molecular catalyst, palladium supported on phosphorus‐doped porous organic polymer exhibits even better catalytic performances than that of its analogue homogeneous catalysts in both carbonylation reactions. Moreover, the catalyst can be easily separated and reused for at least 5 times without significant loss in reactivity. Importantly, the catalyst was highly stable under carbonylation reaction conditions, and no palladium nanoparticle was observed even after the 5th reuse.

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“…Water is a cheap, safe and nontoxic solvent and has thus attracted considerable attention when it is used as a solvent in organic synthesis . Meanwhile, the functionalization of aryl halides is of major importance in the field of modern organic chemistry due to the ubiquity of aromatic and heteroaromatic units . However, the catalytic transformations of aryl halides in water generally require water‐soluble homogeneous catalysts, which suffer from practical problems such as catalyst separation and recycling .…”

Section: Introductionmentioning

confidence: 99%

Urea‐based amphiphilic porous organic polymer‐supported palladium as a reusable catalyst for Suzuki–Miyaura coupling and hydroxycarbonylation reactions in water

Lei

Lan

Zhu

et al. 2018

Applied Organom Chemis

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The development of environmentally friendly heterogeneous catalysts for organic reactions in water is becoming of growing importance for the development of sustainable processes. In this work, a porous organic polymer‐supported palladium catalyst (Pd@UPOP‐1) was successfully fabricated from 3,3′‐diaminobenzidine and methylenediphenyl diisocyanate through a facile urea‐forming condensation reaction. The structure and composition of the catalyst were characterized using several physicochemical methods. Pd@UPOP‐1 was found to possess good porous structure and excellent amphiphilicity. Under mild reaction conditions, the catalyst showed excellent catalytic activity and good substrate compatibility for the Suzuki–Miyaura coupling reaction of aryl bromides, as well as the hydroxycarbonylation reaction of aryl iodides. In addition, the catalyst could be used for several consecutive recycles in both cases.

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Non-noble metal-catalysed carbonylative transformations

Cited by 225 publications

References 178 publications

Base Metal Catalyzed Isocyanide Insertions

Base Metal Catalyzed Isocyanide Insertions

Carbonylative Suzuki coupling and alkoxycarbonylation of aryl halides using palladium supported on phosphorus‐doped porous organic polymer as an active and robust catalyst

Urea‐based amphiphilic porous organic polymer‐supported palladium as a reusable catalyst for Suzuki–Miyaura coupling and hydroxycarbonylation reactions in water

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