The Nef Reaction of Isocyanides
Publication type: Journal Article
Publication date: 2014-03-05
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
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- 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
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Total citations:
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Citations from 2024:
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(10.52%)
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MLA
Cite this
RIS
Copy
TY - JOUR
DO - 10.1055/s-0033-1338596
UR - https://doi.org/10.1055/s-0033-1338596
TI - The Nef Reaction of Isocyanides
T2 - Synthesis
AU - Tron, Gian
AU - Tron, Gian Cesare
AU - El Kaim, Laurent
PY - 2014
DA - 2014/03/05
PB - Georg Thieme Verlag KG
SP - 829-841
IS - 07
VL - 46
SN - 0039-7881
SN - 1437-210X
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2014_Tron,
author = {Gian Tron and Gian Cesare Tron and Laurent El Kaim},
title = {The Nef Reaction of Isocyanides},
journal = {Synthesis},
year = {2014},
volume = {46},
publisher = {Georg Thieme Verlag KG},
month = {mar},
url = {https://doi.org/10.1055/s-0033-1338596},
number = {07},
pages = {829--841},
doi = {10.1055/s-0033-1338596}
}
Cite this
MLA
Copy
Tron, Gian, et al. “The Nef Reaction of Isocyanides.” Synthesis, vol. 46, no. 07, Mar. 2014, pp. 829-841. https://doi.org/10.1055/s-0033-1338596.
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