The Ugi–Smiles and Passerini–Smiles Couplings: A Story About Phenols in Isocyanide‐Based Multicomponent Reactions

Kaı̈m, Laurent El; Grimaud, Laurence

doi:10.1002/ejoc.201402783

Cited by 72 publications

(31 citation statements)

References 75 publications

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“…1 Reactions of isocyanides with secondary amines and aldehydes/ketones represent a special case, as the prototypical Mumm rearrangement cannot take place. 2 …”

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confidence: 99%

An Ugi Reaction Incorporating a Redox-Neutral Amine C–H Functionalization Step

Zhu

Seidel

2016

Org. Lett.

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“…1 Reactions of isocyanides with secondary amines and aldehydes/ketones represent a special case, as the prototypical Mumm rearrangement cannot take place. 2 …”

mentioning

confidence: 99%

An Ugi Reaction Incorporating a Redox-Neutral Amine C–H Functionalization Step

Zhu

Seidel

2016

Org. Lett.

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“…As with the original iMCRs, either aldehydes or imines participate leading to the Passerini–Smiles and Ugi–Smiles iMCRs, respectively (Scheme ). The El Kaïm laboratory has established both processes as powerful routes for the production of functionalized heteroaromatic amine ( 44 , Ugi) and phenolic (46, Passerini) products with obvious relevance to medicinal chemistry …”

Section: Two‐electron Smiles Rearrangementmentioning

confidence: 99%

“…The El Kaïml aboratory has established both processes as powerful routes for the production of functionalized heteroaromatic amine (44,U gi)a nd phenolic (46, Passerini)p roducts with obvious relevance to medicinal chemistry. [23]…”

Section: Isocyanide Multicomponent Reactions (Imcr)mentioning

confidence: 99%

Modern Aspects of the Smiles Rearrangement

Holden

Greaney

2017

Chemistry A European J

165

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The Smiles rearrangement is an intramolecular S Ar reaction, breaking a C-X single bond and forming a new C-X or C-C bond though ipso substitution. Its vast scope, in terms of nucleophile, leaving group, and ring-size of the transition state, make it a powerful tool for arene functionalization, as it can be employed strategically to switch easily-forged bonds with more difficult connections that would be challenging to realize in the intermolecular mode. The reaction has received significantly renewed attention in recent years, as advances in areas such as arene C-X bond formation and radical generation have been harnessed for new arene syntheses through Smiles chemistry. In addition, new reaction modes have been discovered, such as the Clayden rearrangement of lithiated ureas, creating innovative applications for Smiles rearrangements in asymmetric arylation. This Minireview will discuss advances in these areas in the recent literature, covering both two-electron, polar Smiles rearrangements along with single-electron radical transformations.

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“…11 As reações multicomponentes que utilizam isonitrilas (isocyanide-based multicomponent reactions, IMCRs) como um dos materiais de partida são particularmente interessantes, devido à disponibilidade comercial de várias isonitrilas e à grande variedade de transformações possíveis de serem realizadas com estes compostos. 12 O grupo -NC apresenta uma reatividade química muito peculiar, conferindo à molécula um sítio nucleofílico e outro eletrofílico. Por esse motivo, as isonitrilas estão presentes em um grande número de reações multicomponentes conhecidas até hoje e surgidas após os trabalhos pioneiros de Passerini 13 e Ugi 14 (Figura 1).…”

Section: Introductionunclassified