26385-07-9Relevant academic research and scientific papers
Dual H-bond activation of NHC-Au(i)-Cl complexes with amide functionalized side-arms assisted by H-bond donor substrates or acid additives
Sepp?nen, Otto,Aikonen, Santeri,Muuronen, Mikko,Alamillo-Ferrer, Carla,Burés, Jordi,Helaja, Juho
supporting information, p. 14697 - 14700 (2020/12/02)
Novel approach with amide-tethered H-bond donor NHC ligands enabled Au(i)-catalysis via H-bonding. The plain NHC-Au(i)-Cl complex catalysed conversions of terminal N-propynamides to oxazolines, and enyne cycloisomerization with an acid additive, in DCM at
Chemoselective Synthesis of α-Amino-α-cyanophosphonates by Reductive Gem-Cyanation-Phosphonylation of Secondary Amides
Chen, Ting-Ting,Wang, Ai-E,Huang, Pei-Qiang
supporting information, p. 3808 - 3812 (2019/05/24)
A novel approach to α-amino-α-cyanophosphonates has been developed. The method features a Tf2O-mediated reductive geminal cyanation/phosphonylation of secondary amides. Mild reaction conditions, high bond-forming efficiency, inexpensive readily available starting materials, and good to excellent yields with wide functional group compatibility constitute the main advantages of this method. The protocol can be run on a gram scale.
One-pot triflic anhydride-mediated synthesis of 1,2-disubstituted 2-imidazolines from N-(2-haloethyl)amides and amines
Ellsworth, Alyssa A.,Magyar, Christina L.,Hubbell, Grace E.,Theisen, Chelsea C.,Holmes, Daniel,Mosey, R. Adam
, p. 6380 - 6389 (2016/09/23)
A one-pot synthesis of 1,2-disubstituted 2-imidazolines from N-(2-haloethyl)amides has been developed. The reaction affords high yields of diverse 1,2-disubstituted 2-imidazolines from triflic anhydride-mediated dehydration of amides followed by installat
Sulfonimidation via ring-opening of 2-oxazolines with acidic sulfonimide nucleophiles
Gutierrez, David A.,Dean, Dayton R.,Laxamana, Candace M.,Migliozzi-Smith, Madyson,O'Brien, Connor J.,O'Neill, Claire L.,Li, Jie Jack
, p. 261 - 276 (2016/07/06)
Acidic sulfonimide nucleophiles including dibenzenesulfonimide, o-benzenesulfonimide, dimethanesulfonimide, and N-(methylsulfonyl)-benzenesulfonamide are discovered to open a variety of alkyl-, aryl- and heteroaryl-2-oxazoline rings to provide the sulfonimidation products in refluxing 1,4-dioxane. The electron-rich 2-oxazoline substrates worked well for the nucleophilic ring-opening reactions while no reaction took place for the electron-poor 2-oxazoline substrates.
METHOD OF CONVERTING ALCOHOL TO HALIDE
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Page/Page column 51; 172; 175, (2017/01/02)
The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.
Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers
Huy, Peter H.,Motsch, Sebastian,Kappler, Sarah M.
supporting information, p. 10145 - 10149 (2016/08/16)
A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.
NHC-amide donor ligands in rhodium complexes: Syntheses and characterisation
Warsink, Stefan,Venter, Johan A.,Roodt, Andreas
, p. 195 - 201 (2015/02/19)
Rhodium(I) complexes bearing amide-functionalised NHC ligands were synthesized in high yields through various synthetic routes and from different metal precursors, showing the versatility of such systems. By changing the ancillary ligands on the rhodium f
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.
Iron-catalyzed efficient synthesis of amides from aldehydes and amine hydrochloride salts
Ghosh, Subhash Chandra,Ngiam, Joyce S. Y.,Chai, Christina L. L.,Seayad, Abdul M.,Dang, Tuan Thanh,Chen, Anqi
supporting information; experimental part, p. 1407 - 1412 (2012/07/13)
A practical and efficient method for the synthesis of amides has been developed by iron-catalysed oxidative amidation of aldehydes with amine hydrochloride salts. A wide range of amides have been obtained in good to excellent yields under mild conditions. The application of this novel amide formation reaction to the synthesis of pharmaceutical compounds has been successfully demonstrated. Copyright
