The Nef reaction of isocyanides

Fabio La Spisa; Gian Cesare Tron; Laurent El Kaïm

doi:10.1055/s-0033-1338596

The Nef reaction of isocyanides

Fabio La Spisa
, Gian Cesare Tron
, Laurent El Kaïm

Laboratory of Molecular Pathology
Laboratoire de Synthèse Organique

Résultats de recherche: Contribution à un journal › Article de révision › Revue par des pairs

Résumé

The interaction of isocyanides with acyl chlorides was first reported by Nef in 1892. The resulting α-keto imidoyl chlorides may be hydrolyzed to form α-keto amides. Relatively few data are available on this reaction and the chemistry of α-keto imidoyl chlorides has been largely underestimated until some recent uses in intraÂ- and intermolecular couplings with a variety of nucleophiles. The present review brings a comprehensive presentation of the Nef reaction of isocyanides focusing on mechanism and regioselectivity issues. 1 Isocyanide Chemistry 2 Isocyanide Interaction with Acyl Chlorides and Analogues 2.1 General Considerations 2.2 Methods of Preparation of α-Keto Imidoyl Chlorides 2.3 Nef Reaction Mechanism 3 Reactivity of α-Keto Imidoyl Chlorides 3.1 General Behavior of α-Keto Imidoyl Chlorides 3.2 Intramolecular Trappings 3.3 Intermolecular Trappings and Three-Component Reactions 4 Extensions of the Nef Reaction 5 Conclusion

langue originale	Anglais
Numéro d'article	4068
Pages (de - à)	829-841
Nombre de pages	13
journal	Synthesis
Volume	46
Numéro de publication	7
Les DOIs	https://doi.org/10.1055/s-0033-1338596
état	Publié - 1 janv. 2014
Modification externe	Oui

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10.1055/s-0033-1338596

Contient cette citation

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title = "The Nef reaction of isocyanides",

abstract = "The interaction of isocyanides with acyl chlorides was first reported by Nef in 1892. The resulting α-keto imidoyl chlorides may be hydrolyzed to form α-keto amides. Relatively few data are available on this reaction and the chemistry of α-keto imidoyl chlorides has been largely underestimated until some recent uses in intra{\^A}- and intermolecular couplings with a variety of nucleophiles. The present review brings a comprehensive presentation of the Nef reaction of isocyanides focusing on mechanism and regioselectivity issues. 1 Isocyanide Chemistry 2 Isocyanide Interaction with Acyl Chlorides and Analogues 2.1 General Considerations 2.2 Methods of Preparation of α-Keto Imidoyl Chlorides 2.3 Nef Reaction Mechanism 3 Reactivity of α-Keto Imidoyl Chlorides 3.1 General Behavior of α-Keto Imidoyl Chlorides 3.2 Intramolecular Trappings 3.3 Intermolecular Trappings and Three-Component Reactions 4 Extensions of the Nef Reaction 5 Conclusion",

keywords = "Nef reaction, acyl chlorides, imidoyl chlorides, isocyanides, ketenes",

author = "\{La Spisa\}, Fabio and Tron, \{Gian Cesare\} and \{El Ka{\"i}m\}, Laurent",

year = "2014",

month = jan,

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doi = "10.1055/s-0033-1338596",

language = "English",

volume = "46",

pages = "829--841",

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TY - JOUR

T1 - The Nef reaction of isocyanides

AU - La Spisa, Fabio

AU - Tron, Gian Cesare

AU - El Kaïm, Laurent

PY - 2014/1/1

Y1 - 2014/1/1

N2 - The interaction of isocyanides with acyl chlorides was first reported by Nef in 1892. The resulting α-keto imidoyl chlorides may be hydrolyzed to form α-keto amides. Relatively few data are available on this reaction and the chemistry of α-keto imidoyl chlorides has been largely underestimated until some recent uses in intraÂ- and intermolecular couplings with a variety of nucleophiles. The present review brings a comprehensive presentation of the Nef reaction of isocyanides focusing on mechanism and regioselectivity issues. 1 Isocyanide Chemistry 2 Isocyanide Interaction with Acyl Chlorides and Analogues 2.1 General Considerations 2.2 Methods of Preparation of α-Keto Imidoyl Chlorides 2.3 Nef Reaction Mechanism 3 Reactivity of α-Keto Imidoyl Chlorides 3.1 General Behavior of α-Keto Imidoyl Chlorides 3.2 Intramolecular Trappings 3.3 Intermolecular Trappings and Three-Component Reactions 4 Extensions of the Nef Reaction 5 Conclusion

AB - The interaction of isocyanides with acyl chlorides was first reported by Nef in 1892. The resulting α-keto imidoyl chlorides may be hydrolyzed to form α-keto amides. Relatively few data are available on this reaction and the chemistry of α-keto imidoyl chlorides has been largely underestimated until some recent uses in intraÂ- and intermolecular couplings with a variety of nucleophiles. The present review brings a comprehensive presentation of the Nef reaction of isocyanides focusing on mechanism and regioselectivity issues. 1 Isocyanide Chemistry 2 Isocyanide Interaction with Acyl Chlorides and Analogues 2.1 General Considerations 2.2 Methods of Preparation of α-Keto Imidoyl Chlorides 2.3 Nef Reaction Mechanism 3 Reactivity of α-Keto Imidoyl Chlorides 3.1 General Behavior of α-Keto Imidoyl Chlorides 3.2 Intramolecular Trappings 3.3 Intermolecular Trappings and Three-Component Reactions 4 Extensions of the Nef Reaction 5 Conclusion

KW - Nef reaction

KW - acyl chlorides

KW - imidoyl chlorides

KW - isocyanides

KW - ketenes

U2 - 10.1055/s-0033-1338596

DO - 10.1055/s-0033-1338596

M3 - Review article

AN - SCOPUS:84897098776

SN - 0039-7881

VL - 46

SP - 829

EP - 841

JO - Synthesis

JF - Synthesis

IS - 7

M1 - 4068

ER -

The Nef reaction of isocyanides

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