ChemInform Abstract: PALLADIUM‐CATALYZED DOUBLE CARBONYLATION OF ARYL HALIDES TO GIVE α‐KETO AMIDES. MECHANISTIC STUDIES

Ozawa, Fumiyuki; Soyama, Hidehiko; Yanagihara, Hisayoshi; Aoyama, Issei; Takino, H.; Izawa, K.; Yamamoto, Takashi; Yamamoto, Akio

doi:10.1002/chin.198538152

Cited by 2 publications

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“…Inoue and co-workers 247 found that the same reaction could be efficiently carried out using the chloro-bridged homobime-tallic (palladium) complex Pd 2 Me 2 (μ-Cl)(μ-dpfam) (Figure 21). Although the trends were similar to those obtained under mononuclear catalysis, 240 both reaction efficiency (total yield) and selectivity (di/monocarbonylation products ratio) were improved. Thus, acyclic secondary amines were suitable for the reaction, while pyrrolidine and piperidine showed high reactivity with moderate selectivity (Table 1).…”

Section: Palladium-catalyzed Double-carbonylative Aminationsupporting

confidence: 71%

Recent Developments in General Methodologies for the Synthesis of α-Ketoamides

2016

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The α-ketoamide motif is widely found in many natural products and drug candidates with relevant biological activities. Furthermore, α-ketoamides are attractive candidates to synthetic chemists due to the ability of the motif to access a wide range of functional group transformations, including multiple bond-forming processes. For these reasons, a vast array of synthetic procedures for the preparation of α-ketoamides have been developed over the past decades, and the search for expeditious and efficient protocols continues unabated. The aim of this review is to give an overview of the diverse methodologies that have emerged since the 1990s up to the present. The different synthetic routes have been grouped according to the way the α-ketoamide moiety has been created. Thus, syntheses of α-ketoamides proceeding via C(2)-oxidation of amide starting compounds are detailed, as are amidation approaches installing the α-ketoamide residue through C(1)-N bond formation. Also discussed are the methodologies centered on C(1)-C(2) σ-bond construction and C(2)-R/Ar bond-forming processes. Finally, the literature regarding the synthesis of α-ketoamide compounds by palladium-catalyzed double-carbonylative amination reactions is discussed.

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Section: Palladium-catalyzed Double-carbonylative Aminationsupporting

confidence: 71%