Trisulfur-Radical-Anion-Triggered C(sp2)-H Amination of Electron-Deficient Alkenes
A trisulfur-radical-anion (S3˙-)-triggered C(sp2)-H amination of α,β-unsaturated carbonyl derivatives with simple amines has been demonstrated. This protocol provides convenient access to a variety of synthetically valuable N-unprotected and secondary β-enaminones with absolute Z selectivity and tertiary β-enaminones with E selectivity. Mechanistic probe and electronic structure theory calculations suggest that S3˙- initiates the nucleophilic attacks via a thiirane intermediate.
Nguyen, Khang X.,Nguyen, Thao T.,Nguyen, Tung T.,Pham, Hoai T. B.,Pham, Phuc H.,Phan, Nam T. S.,Wang, Haobin,Yang, Chou-Hsun
supporting information
p. 9751 - 9756
(2020/12/21)
Reactions of enamines with selectfluor: A straightforward route to difluorinated carbonyl compounds
Reactions of enamines, preformed from β-dicarbonyl and monocarbonyl compounds, with Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2] octane bis(tetrafluoroborate) under mild conditions (triethylamine (TEA) or molecular sieves) easily led to the corresponding difluorinated carbonyl compounds in high yields.
Peng, Weimin,Shreeve, Jean'ne M.
p. 5760 - 5763
(2007/10/03)
Straightforward Novel One-Pot Enaminone and Pyrimidine Syntheses by Coupling-Addition-Cyclocondensation Sequences
The coupling of acid chlorides 1 with terminal alkynes 2 using only one equivalent (!) of triethylamine under Sonogashira conditions followed by subsequent addition of primary or secondary amines 4 to the intermediate alkynones 3 represents a straight-for
Karpov, Alexei S.,Mueller, Thomas J. J.
p. 2815 - 2826
(2007/10/03)
Synthesis in dry media coupled with microwave irradiation: Application to the preparation of enaminoketones
β-diketones react with a variety of amines and aminoesters over clay K10 or silica under microwave irradiation in open vessels to give within a few minutes, the corresponding enaminoketones with good yields. According to the reaction conditions acylamines may also result.
Rechsteiner,Texier-Boullet,Hamelin
p. 5071 - 5074
(2007/10/02)
More Articles about upstream products of 145800-06-2