Highly efficient Markovnikov hydroaminocarbonylation of alkenes and alkynes catalyzed by a “soluble” heterogeneous Pd catalyst

Zhou, Xin; Wang, Zhaozhan; Chen, Yuanfu; Kuang, Shaoping; Sun, Wei; Yang, Yong

doi:10.1039/d2gc00815g

Cited by 14 publications

(5 citation statements)

References 61 publications

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Section: Construction Of C=o Bondmentioning

confidence: 99%

“…It is notable that some researchers have shown a keen interest in green chemistry, leading to significant advancements, mainly centered around the use of recoverable solvents [194] and unconventional heterogeneous catalysts. [195] When alkenes serve as substrates, the typical initial step involves hydrometallation. Consequently, the formation of two isomeric intermediates (and products) emerges as an area of concern.…”

Section: Carbonyl Insertionmentioning

confidence: 99%

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Contemporary Approaches for Amide Bond Formation

Acosta‐Guzmán,

Ojeda‐Porras,

Gamba‐Sánchez

2023

Adv Synth Catal

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Amide bond construction has garnered significant interest in recent decades due to amides being one of the most prevalent functional groups among bioactive molecules. Out of the thirty‐seven new drugs approved by the FDA in 2022, eleven are small molecules containing at least one amide bond. Additionally, there are nineteen large molecules approved as new drugs, some of which have peptide structures, and therefore, also bear amide bonds. In recent years, multiple teams have embraced the challenge of developing more efficient methods for amide bond formation. This dedication has led to numerous publications appearing monthly in prestigious journals, showcasing significant advancements in this field. The primary goal of this review is to present the most viable strategies for constructing the amide bond. It is crucial to differentiate between amide bond formation and amide synthesis; hence, the focus is on describing specific methods for forming new C(O)−N bonds. In particular, this review concentrates on the methods developed within the last six years. There is a particular emphasis on new approaches that consider the thought process when selecting the starting materials and functional groups. This approach ensures coverage of all the most common chemical transformations that yield new amide bonds.

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Section: Construction Of C=o Bondmentioning

confidence: 99%

Section: Carbonyl Insertionmentioning

confidence: 99%

Contemporary Approaches for Amide Bond Formation

Acosta‐Guzmán,

Ojeda‐Porras,

Gamba‐Sánchez

2023

Adv Synth Catal

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“…During the last two decades, extensive investigations have been made regarding transition-metal catalysts, the scope of alkynes and nucleophiles, and the regioselectivity for unsymmetrical alkynes. 4,5 For example, Wu's group have recently achieved ligand-controlled regioselective hydrothiocarbonylation of terminal alkynes 5 v and the more challenging regio- and stereoselective hydroaminocarbonylation of unsymmetrical internal alkynes. 5 x Beller also reported regio- and stereoselective hydroaminocarbonylation of unsymmetrical 1,3-diynes by exploiting the interactions of ligands with substrates.…”

Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed alkyne hydrocarbonylation under atmospheric pressure of carbon monoxide in the presence of hydrosilane

et al. 2023

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“…Pd heterogeneous catalysts that are readily processed facilitate practical applications, ,− and solution processing is generally preferred for the immobilization of heterogeneous catalysts . However, the polymer-supported catalysts should be intrinsically insoluble in the reaction solvents or made to be insoluble by cross-linking of films/particles.…”

Section: Introductionmentioning

confidence: 99%

Versatile Nanoporous Organic Polymer Catalyst for the Size-Selective Suzuki–Miyaura Coupling Reaction

Guo

Luo

et al. 2022

ACS Appl. Nano Mater.

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Heterogenous catalysts with confined nanoporous catalytic sites are shown to have high activity and size selectivity. A solution-processable nanoporous organic polymer (1-BPy-Pd) catalyst displays high catalytic performance (TON > 200K) in the heterogeneous Suzuki–Miyaura coupling (SMC) reaction and can be used for the preparation of the intermediates in the synthesis of pharmaceutical agents. In comparison to the homogeneous catalyst analogue (2,2′-BPy)PdCl2, the heterogenous system offers size-dependent catalytic activity when bulkier substrates are used. Furthermore, the catalyst can be used to create catalytic impellers that simplify its use and recovery. We found that this system also works for applications in heterogenous Heck and nitroarenes reduction reactions. The metal-binding nanoporous polymer reported here represents a versatile platform for size-selective heterogeneous and recyclable catalysts.

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Highly efficient Markovnikov hydroaminocarbonylation of alkenes and alkynes catalyzed by a “soluble” heterogeneous Pd catalyst

Abstract: Highly efficient and regioselective synthesis of amides from simple starting materials remains a great challenge. Herein, we reported a highly efficient hydroaminocarbonylation of alkenes and alkynes with amines and CO...

Cited by 14 publications

References 61 publications

Contemporary Approaches for Amide Bond Formation

Contemporary Approaches for Amide Bond Formation

Palladium-catalyzed alkyne hydrocarbonylation under atmospheric pressure of carbon monoxide in the presence of hydrosilane

Versatile Nanoporous Organic Polymer Catalyst for the Size-Selective Suzuki–Miyaura Coupling Reaction

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