138119-50-3Relevant academic research and scientific papers
Amide Synthesis by Nickel/Photoredox-Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides
Alandini, Nurtalya,Buzzetti, Luca,Candish, Lisa,Collins, Karl D.,Favi, Gianfranco,Melchiorre, Paolo,Schulte, Tim
supporting information, p. 5248 - 5253 (2020/03/03)
Herein, we report a one-electron strategy for catalytic amide synthesis that enables the direct carbamoylation of (hetero)aryl bromides. This radical cross-coupling approach, which is based on the combination of nickel and photoredox catalysis, proceeds at ambient temperature and uses readily available dihydropyridines as precursors of carbamoyl radicals. The method's mild reaction conditions make it tolerant of sensitive-functional-group-containing substrates and allow the installation of an amide scaffold within biologically relevant heterocycles. In addition, we installed amide functionalities bearing electron-poor and sterically hindered amine moieties, which would be difficult to prepare with classical dehydrative condensation methods.
Magnetic CuFe2O4nanoparticles: A retrievable catalyst for oxidative amidation of aldehydes with amine hydrochloride salts
Suresh Kumar,Thulasiram,Bala Laxmi,Rawat, Vikas S.,Sreedhar
supporting information, p. 6059 - 6067 (2014/12/10)
The application of magnetic CuFe2O4nanoparticles for the oxidative amidation of aldehydes with amine hydrochloride salts is described. A wide range of amides have been synthesized in good to excellent yields under mild conditions. Chiral amide also synthesized from its corresponding chiral amine salt with retention of the stereochemistry. In particular, the performance of the magnetic separation of the catalyst was very efficient and an alternative to time, solvent and energy-consuming separation procedures. The catalytic activity of the catalyst remains unaltered after five consecutive cycles, making it environmentally benign and widely applicable due to its efficiency, ease of handling and cost effectiveness.
Magnetic CuFe2O4 nanoparticles: A retrievable catalyst for oxidative amidation of aldehydes with amine hydrochloride salts
Suresh Kumar,Thulasiram,Bala Laxmi,Rawat, Vikas S.,Sreedhar
supporting information, p. 6059 - 6067 (2015/03/30)
The application of magnetic CuFe2O4 nanoparticles for the oxidative amidation of aldehydes with amine hydrochloride salts is described. A wide range of amides have been synthesized in good to excellent yields under mild conditions. Chiral amide also synthesized from its corresponding chiral amine salt with retention of the stereochemistry. In particular, the performance of the magnetic separation of the catalyst was very efficient and an alternative to time, solvent and energy-consuming separation procedures. The catalytic activity of the catalyst remains unaltered after five consecutive cycles, making it environmentally benign and widely applicable due to its efficiency, ease of handling and cost effectiveness.
Copper-catalyzed oxidative amidation of aldehydes with amine salts: Synthesis of primary, secondary, and tertiary amides
Ghosh, Subhash Chandra,Ngiam, Joyce S. Y.,Seayad, Abdul M.,Tuan, Dang Thanh,Chai, Christina L. L.,Chen, Anqi
, p. 8007 - 8015,9 (2012/12/12)
A practical method for the amidation of aldehydes with economic ammonium chloride or amine hydrochloride salts has been developed for the synthesis of a wide variety of amides by using inexpensive copper sulfate or copper(I) oxide as a catalyst and aqueous tert-butyl hydroperoxide as an oxidant. This amidation reaction is operationally straightforward and provides primary, secondary, and tertiary amides in good to excellent yields for most cases utilizing inexpensive and readily available reagents under mild conditions. In situ formation of amine salts from free amines extends the substrate scope of the reaction. Chiral amides are also synthesized from their corresponding chiral amines without detectable racemization. The practicality of this amide formation reaction has been demonstrated in an efficient synthesis of the antiarrhythmic drug N-acetylprocainamide.
Copper-catalyzed oxidative amidation of aldehydes with amine salts: Synthesis of primary, secondary, and tertiary amides
Ghosh, Subhash Chandra,Ngiam, Joyce S.Y.,Seayad, Abdul M.,Tuan, Dang Thanh,Chai, Christina L.L.,Chen, Anqi
, p. 8007 - 8015 (2013/01/15)
A practical method for the amidation of aldehydes with economic ammonium chloride or amine hydrochloride salts has been developed for the synthesis of a wide variety of amides by using inexpensive copper sulfate or copper(I) oxide as a catalyst and aqueous tert-butyl hydroperoxide as an oxidant. This amidation reaction is operationally straightforward and provides primary, secondary, and tertiary amides in good to excellent yields for most cases utilizing inexpensive and readily available reagents under mild conditions. In situ formation of amine salts from free amines extends the substrate scope of the reaction. Chiral amides are also synthesized from their corresponding chiral amines without detectable racemization. The practicality of this amide formation reaction has been demonstrated in an efficient synthesis of the antiarrhythmic drug N-acetylprocainamide.
Titanium-catalyzed stereoselective synthesis of spirooxindole oxazolines
Badillo, Joseph J.,Arevalo, Gary E.,Fettinger, James C.,Franz, Annaliese K.
supporting information; experimental part, p. 418 - 421 (2011/04/15)
A regio-and stereoselective cyclization between isatins and 5-methoxyoxazoles has been developed using catalytic titanium (IV) chloride (10 or 20 mol %) to afford spiro[3,3'-oxindoleoxazolines] in excellent yield (up to 99%) and diastereoselectivity (dr >
Synthesis and structural characterization of amino acid and peptide derivatives featuring N-(p-bromobenzoyl) substituents as promising connection unit for bio-inspired hybrid compounds
Ei?mann, Frank,Weber, Edwin
, p. 392 - 402 (2011/08/03)
Using a sequence of activation, blocking and peptide coupling procedures, a series of ten amino acid and peptide derivatives 1-6 (a, b, respectively) featuring a p-bromobenzoyl substituent attached to the amino group of the parent compound has been synthe
Neutral peptide biradicals formed by dissociative electron transfer
Burns, Colin S.,Rochelle, Lakecia,Forbes, Malcolm D. E.
, p. 2197 - 2199 (2007/10/03)
(Matrix presented) A new method for the generation of transient neutral biradicals in liquid solution is reported. Photoinduced electron transfer in aqueous solution of the structures shown above leads to neutral biradicals with peptide spacers. Exchange
