Triphenylphosphine promoted regio and stereoselective α-halogenation of ynamides‡
Literature Information
Publication Date
2015-11-30
DOI
10.1039/C5QO00345H
Impact Factor
5.281
Authors
B. Prabagar, Sanatan Nayak, Rajendra K. Mallick, Rangu Prasad, Akhila K. Sahoo
View Original
Abstract
In this study, we demonstrate metal free regio- and stereoselective α-halogenation (Cl, Br and I) of ynamides. The halogenation of ynamides in the presence of PPh3 and CCl4, CBr4 or CHI3 in moist CH2Cl2 at room temperature provides good-to-excellent yields of a wide variety of stable (E)-α-haloenamides; thus, the reaction has a broad scope. Chlorination of ynamides at room temperature is particularly notable. The sequential one pot α-iodination and alkynylation of ynamides provide synthetically useful amidoenynes. The chlorination of 3-acetoxy ynamide delivers 3-acetoxy-α-chloro enamide without the migratory-assistance of the acetoxy moiety.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![tert-Butyl 6-chloro-4-oxospiro[chroman-2,4'-piperidine]-1'-carboxylate structure](https://static.chemtradehub.com/structs/101/1011482-37-3-88a5.webp "tert-Butyl 6-chloro-4-oxospiro[chroman-2,4'-piperidine]-1'-carboxylate structure")
tert-Butyl 6-chloro-4-oxospiro[chroman-2,4'-piperidine]-1'-carboxylate
CAS Number:
1011482-37-3
Molecular Formula:
C18H22ClNO4
1-(3,4-Dichlorophenyl)-1H-pyrazole-3-carboxylic acid
CAS Number:
1152949-12-6
Molecular Formula:
C10H6Cl2N2O2
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