Metal‐Catalyzed Multicomponent Reactions

Balme, Geneviève; Bouyssi, Didier; Monteiro, Nuno

doi:10.1002/3527605118.ch8

Cited by 32 publications

(15 citation statements)

References 116 publications

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“…The unique features of transition metal-catalyzed reactions contributed to the rising popularity of transition metalcatalyzed MCRs. 50 Transition metal-catalyzed MCRs have been incorporated into various reaction sequences achieving impressive diversity in the resulting molecular ensembles. The effort to perform the sequential reactions as one-pot procedures brought attention to an emerging challenge of identifying reaction conditions that would avoid undesired interactions between the components of the multicatalytic systems.…”

Section: Transition Metal-catalyzed Mcrs In Sequential Protocolsmentioning

confidence: 99%

Recent advances in the discovery and design of multicomponent reactions for the generation of small-molecule libraries

Malinakova¹

2015

ROC

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The current drug discovery process is dependent on the ability of synthetic chemistry to deliver libraries of small molecules with ever increasing levels of structural complexity and diversity. Sequencing multicomponent reactions (MCRs) with elaboration or cyclization steps represents an effective approach toward generating libraries of complex and diverse small molecules. This review highlights the most recent (2010-2015) examples of the application of reaction sequences including MCRs to the synthesis of diverse assemblies of small heterocycles. Sequences performed in multiple separate steps, or as one-pot operations, and including MCRs based on 1) carbonyl condensations; 2) isocyanide-based reactions; 3) cycloadditions; and 4) transition metal-mediated reactions are discussed.

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Section: Transition Metal-catalyzed Mcrs In Sequential Protocolsmentioning

confidence: 99%

Recent advances in the discovery and design of multicomponent reactions for the generation of small-molecule libraries

Malinakova¹

2015

ROC

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“…Using Pd(OAc) 2 (at higher loading) instead of Pd 2 (dba) 3 as a pre-catalyst improved the yield of 1a to 41% (entry 11). Among the bases investigated, Cs 2 CO 3 was found to be far superior to K 3 PO 4 and KO t Bu as the latter bases failed to promote the N-arylation reaction under otherwise identical conditions (entries [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

“…2). 11 The N-arylation of N-alkylpropiolamide 3 is unprecedented in the literature. 12 Indeed, two competitive reactions, N-arylation and carbopalladation, can take place when haloarene 2 and Nalkylpropiolamide 3 are reacted in the presence of a given palladium catalyst.…”

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confidence: 99%

Palladium-catalyzed domino N-arylation/carbopalladation/C–H functionalization: three-component synthesis of 3-(diarylmethylene)oxindoles

Pinto

Neuville

Zhu

2009

Tetrahedron Letters

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“…We have previously reported a palladium-catalyzed multicomponent synthesis of imidazolinium carboxylates from imines, acid chlorides and CO ( Scheme 1 ) [ 25 , 26 , 27 ]. Transition-metal catalyzed multicomponent reactions have emerged as a powerful tool in synthesis as they can allow the controlled assembly of multiple simple units directly into complex products [ 28 , 29 , 30 , 31 , 32 , 33 ]. The generation of 1 proceeds via imine cycloaddition to an in situ generated münchnone ( Scheme 1 ).…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides

Worrall

Arndtsen

2012

Molecules

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We describe the palladium-catalyzed multicomponent synthesis of 2-imidazolines. This reaction proceeds via the coupling of imines, acid chlorides and carbon monoxide to form imidazolinium carboxylates, followed by a decarboxylation. Decarboxylation in CHCl3 is found to result in a mixture of imidazolinium and imidazolium salts. However, the addition of benzoic acid suppresses aromatization, and generates the trans-disubstituted imidazolines in good yield. Combining this reaction with subsequent nitrogen deprotection provides an overall synthesis of imidazolines from multiple available building blocks.

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Metal‐Catalyzed Multicomponent Reactions

Cited by 32 publications

References 116 publications

Recent advances in the discovery and design of multicomponent reactions for the generation of small-molecule libraries

Recent advances in the discovery and design of multicomponent reactions for the generation of small-molecule libraries

Palladium-catalyzed domino N-arylation/carbopalladation/C–H functionalization: three-component synthesis of 3-(diarylmethylene)oxindoles

Palladium-Catalyzed Multicomponent Synthesis of 2-Imidazolines from Imines and Acid Chlorides

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