95602-06-5Relevant academic research and scientific papers
Intramolecular Aminoazidation of Unactivated Terminal Alkenes by Palladium-Catalyzed Reactions with Hydrogen Peroxide as the Oxidant
Beccalli, Egle M.,Broggini, Gianluigi,Foschi, Francesca,Lo Presti, Leonardo,Loro, Camilla,Oble, Julie,Poli, Giovanni,Sala, Roberto
supporting information, (2020/02/28)
The palladium-catalyzed aminoazidation of aminoalkenes yielding azidomethyl-substituted nitrogen-containing heterocycles was developed. The procedure requires oxidative conditions and occurs at room temperature in the presence of hydrogen peroxide and NaN3 as the azide source. These conditions provide selective exo-cyclization/azidation of the carbon-carbon double bond, furnishing a versatile approach toward five-, six-, and seven-membered heterocyclic rings.
A palladium-catalyzed aminoalkynylation strategy towards bicyclic heterocycles: Synthesis of (±)-trachelanthamidine
Nicolai, Stefano,Piemontesi, Cyril,Waser, Jerome
supporting information; experimental part, p. 4680 - 4683 (2011/06/23)
Sweet cyclizations: The synthesis of pyrrolizidines and indolizidines has been achieved. Olefins were subjected to an intramolecular palladium-catalyzed aminoalkynylation with the hypervalent iodine reagent TIPS-EBX. After removal of the protecting group, a two-step cyclization sequence and subsequent reduction led to the natural product (±)-trachelanthamidine (see scheme; TIPS-EBX=triisopropylsilyl ethynylbenziodoxolone).
Copper-catalyzed N-Allenylation of allylic sulfonamides
Persson, Andreas K. A.,Johnston, Eric V.,Baeckvall, Jan-E.
supporting information; experimental part, p. 3814 - 3817 (2009/12/06)
Figur Presented Allylic allenic amides have been synthesized via a copper-catalyzed cross-coupling between allylic sulfonamides and bromoallenes in moderate to good yields. Copper(I) thiophene-2-carboxylate (CuTC) was used a source of copper with DMEDA as the ligand. The allenylated products obtained are potential substrates for palladium-catalyzed carbocyclizations.
A facile highly regio- and stereoselective preparation of N-tosyl allylic amines from allylic alcohols and tosyl isocyanate via palladium(II)-catalyzed aminopalladation-β-heteroatom elimination
Lei, Aiwen,Lu, Xiyan
, p. 2357 - 2360 (2007/10/03)
(equation presented) The high regio- and stereoselectivity have been obtained from the allylic substitution reaction catalyzed by palladium(II) species. From allylic alcohols, one-pot reaction with tosyl isocyanate followed by palladium(II)-catalyzed ally
Palladium(II)-Catalyzed Intramolecular Aminocarbonylation of endo-Carbamates under Wacker-Type Conditions
Harayama, Hiroto,Abe, Atsuhiro,Sakado, Tomonori,Kimura, Masanari,Fugami, Keigo,Tanaka, Shuji,Tamaru, Yoshinao
, p. 2113 - 2122 (2007/10/03)
Pd(II)-catalyzed intramolecular aminocarbonylation of olefins bearing many types of nitrogen nucleophiles has been examined under two typical conditions: acidic conditions [conditions A, typically PdCl2 (0.1 equiv) and CuCl2 (3.0 equiv) under 1 atm of CO at room temperature in methanol] and buffered conditions [conditions B, typically PdCl2 (0.1 equiv) and CuCl2 (2.3 equiv) under 1 atm of CO at 30°C in trimethyl orthoacetate]. Among nitrogen nucleophiles, endocarbamates 7 display distinctive reactivity: endo-carbamates 7a-k smoothly undergo intramolecular aminocarbonylation under conditions B to furnish 4-[(methoxycarbonyl)methyl]-2-oxazolidinones 8a-k in good yields, while they would not undergo the expected reaction under conditions A. Other nitrogen nucleophiles (exo-ureas 1, endo-ureas 3, exo-carbamates 5, and exo-tosylamides 9), on the other hand, satisfactorily undergo aminocarbonylation only under conditions A to give rise to 2,4,6, and 10, respectively, in good yields. Under conditions B, they are unreactive and provide either the expected products in poor yields or intractable mixtures of products. On the basis of this contrasting reactivity between endo-carbamates and other nitrogen nucleophiles, the chemoselective aminocarbonylation of 71-o has been achieved; aminocarbonylation takes place at the endo-carbamate moieties to furnish 81-o exclusively under conditions B, and aminocarbonylation occurs at the exo-carbamate, exo-urea, and exo-tosylamide moieties to yield 13a-d exclusively under conditions A.
