Transamidation of Carboxamides and Amide Derivatives: Mechanistic Insights, Concepts, and Reactions

Acosta‐Guzmán, Paola; Corredor‐Barinas, John; Gamba‐Sánchez, Diego

doi:10.1002/9783527830251.ch6

Cited by 3 publications

(1 citation statement)

References 107 publications

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“…32 The acidic cleavage proceeded smoothly, successfully synthesizing amino pyrazole on a multi-kilogram scale. Transamidation reactions have gained significant importance in organic chemistry, primarily focusing on the synthesis of amides, 33 which have long been regarded as target molecules. However, in recent decades, it has been revealed that amides can also serve as useful synthetic intermediates, leading to an increase in the number of amide bond reactions documented in the literature.…”

Section: Imides and Amidesmentioning

confidence: 99%

Ammonia surrogates in the synthesis of primary amines

Urbiña-Alvarez,

Rincón-Carvajal,

Gamba-Sánchez

2023

Org. Biomol. Chem.

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Section: Imides and Amidesmentioning

confidence: 99%

Ammonia surrogates in the synthesis of primary amines

Urbiña-Alvarez,

Rincón-Carvajal,

Gamba-Sánchez

2023

Org. Biomol. Chem.

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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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Direct synthesis of α-functionalized amides via heteroatom–hydrogen insertion reactions using amide-sulfoxonium ylides

Wu,

Xu,

Lin

et al. 2024

Nat Commun

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α-Functionalized Si-, Ge-, B-, Se-, and S-amide moieties are present in many medicinally active molecules, but their synthesis remains challenging. Here, we demonstrate a high-throughput synthesis using amide-sulfoxonium ylides as carbene precursors in a Si–H, Ge–H, B–H, Se–H, and S–H insertion reactions to target a wide range of α-silyl, α-geryl, α-boryl, α-selenyl, and α-sulfur (hetero)amides. The process is featured as simple operation, mild conditions, broad substrate scope, high functional group compatibility, and excellent chemoselectivity. Both experimental and computational studies are conducted to explore the mechanisms underlying the formation of C–Si/Ge/B/Se/S bond. This research highlights the use of highly selective X–H insertion reactions with amide-sulfoxonium ylide-derived carbenes, paving the way for the preparation of diverse functional organosilane, organogermane, organoboron, organoselenium, and organosulfur compounds from accessible and bench-stable precursors.

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Transamidation of Carboxamides and Amide Derivatives: Mechanistic Insights, Concepts, and Reactions

Cited by 3 publications

References 107 publications

Ammonia surrogates in the synthesis of primary amines

Ammonia surrogates in the synthesis of primary amines

Contemporary Approaches for Amide Bond Formation

Direct synthesis of α-functionalized amides via heteroatom–hydrogen insertion reactions using amide-sulfoxonium ylides

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