Direct defluorinative amidation-hydrolysis reaction of gem-difluoroalkenes with N,N-dimethylformamide, and primary and secondary amines.

A novel and efficient method for the synthesis of arylacetamides by the reactions of gem-difluoroalkenes with N,N-dialkylformamides, and primary and secondary amines with the assistance of KOtBu and water was developed.

[1]  E. Olejniczak,et al.  Discovery of Potent 2-Aryl-6,7-dihydro-5 H-pyrrolo[1,2- a]imidazoles as WDR5-WIN-Site Inhibitors Using Fragment-Based Methods and Structure-Based Design. , 2018, Journal of medicinal chemistry.

[2]  Tohru Yamada,et al.  Amidation reaction of carboxylic acid with formamide derivative using SO3•pyridine , 2018 .

[3]  S. Cao,et al.  Copper- and Nickel-Catalyzed Cross-Coupling Reaction of Monofluoroalkenes with Tertiary, Secondary, and Primary Alkyl and Aryl Grignard Reagents , 2018 .

[4]  W. Su,et al.  Copper-Catalyzed Cyclization for Access to 6H-Chromeno[4,3-b]quinolin-6-ones Employing DMF as the Carbon Source. , 2017, The Journal of organic chemistry.

[5]  Jinbo Hu,et al.  TMSCF3 as a Convenient Source of CF2 =CF2 for Pentafluoroethylation, (Aryloxy)tetrafluoroethylation, and Tetrafluoroethylation. , 2017, Angewandte Chemie.

[6]  S. Cao,et al.  Cu-Catalyzed Stereoselective Borylation of gem-Difluoroalkenes with B2pin2. , 2017, Organic letters.

[7]  S. Cao,et al.  Recent advances in the synthesis and CF functionalization of gem-difluoroalkenes , 2017 .

[8]  T. Hosoya,et al.  Rhodium‐Catalyzed Decarbonylative Borylation of Aromatic Thioesters for Facile Diversification of Aromatic Carboxylic Acids , 2017, Angewandte Chemie.

[9]  M. Sanford,et al.  Iron-Catalyzed Hydrogenation of Amides to Alcohols and Amines , 2016 .

[10]  S. Cao,et al.  Mild and Copper-Free Stereoselective Cyanation of gem-Difluoroalkenes by Using Benzyl Nitrile as a Cyanating Reagent. , 2016, Chemistry.

[11]  P. Bukowska,et al.  A three-component synthesis of aryl(heteroaryl)acylamides. , 2015, Organic & biomolecular chemistry.

[12]  S. Cao,et al.  Copper-Catalyzed Coupling Cyclization of gem-Difluoroalkenes with Activated Methylene Carbonyl Compounds: Facile Domino Access to Polysubstituted Furans. , 2015, Organic letters.

[13]  Yanghui Zhang,et al.  Copper-catalyzed amide bond formation from formamides and carboxylic acids , 2015 .

[14]  A. Baldessari,et al.  Lipase-catalyzed synthesis of substituted phenylacetamides: Hammett analysis and computational study of the enzymatic aminolysis , 2014 .

[15]  J. Ready,et al.  The ketene-surrogate coupling: catalytic conversion of aryl iodides into aryl ketenes through ynol ethers. , 2014, Angewandte Chemie.

[16]  M. Hoffmann,et al.  Tri- and tetrafluoropropionamides derived from chiral secondary amines – synthesis and the conformational studies , 2014 .

[17]  Christina L. L. Chai,et al.  Loperamide-based compounds as additives for biofouling management , 2014 .

[18]  Jianliang Xiao,et al.  DMF as carbon source: Rh-catalyzed α-methylation of ketones. , 2014, Organic letters.

[19]  Yixiang Cheng,et al.  Copper-catalyzed oxidative coupling of carboxylic acids with formamides for the synthesis of α,β-unsaturated amides , 2013 .

[20]  Xiangge Zhou,et al.  Copper-catalyzed formation of N,N-dimethyl benzamide from nitrile and DMF under an O2 atmosphere. , 2013, Organic & biomolecular chemistry.

[21]  M. Kantam,et al.  Copper catalyzed cross-coupling reactions of carboxylic acids: an expedient route to amides, 5-substituted γ-lactams and α-acyloxy esters , 2013 .

[22]  Hua Wang,et al.  Copper-catalyzed oxidative condensation of α-oxocarboxylic acids with formamides: synthesis of α-ketoamides. , 2013, Organic & biomolecular chemistry.

[23]  Lei Wang,et al.  Cu(II)-catalyzed decarboxylative acylation of acyl C-H of formamides with α-oxocarboxylic acids leading to α-ketoamides. , 2013, Chemical communications.

[24]  K. Reddy,et al.  Copper‐Catalyzed Oxidative Coupling of Carboxylic Acids with N,N‐Dialkylformamides: An Approach to the Synthesis of Amides , 2013 .

[25]  Yixiang Cheng,et al.  Metal-free n-Bu4NI-catalyzed direct synthesis of amides from alcohols and N,N-disubstituted formamides , 2012 .

[26]  Helena Lundberg,et al.  Direct Catalytic Formation of Primary and Tertiary Amides from Non‐Activated Carboxylic Acids, Employing Carbamates as Amine Source , 2012 .

[27]  L. Qu,et al.  nBu4NI-catalyzed direct synthesis of α-ketoamides from aryl methyl ketones with dialkylformamides in water using TBHP as oxidant. , 2012, Chemical communications.

[28]  N. Jiao,et al.  N,N-dimethylformamide: a multipurpose building block. , 2012, Angewandte Chemie.

[29]  J. Park,et al.  Chiral Separation on Sulfonated Cellulose Tris(3,5-dimethylphenylcarbamate)-coated Zirconia Monolith by Capillary Electrochromatography , 2012 .

[30]  S. Zhang,et al.  Direct amidation of alcohols with N-substituted formamides under transition-metal-free conditions. , 2012, Chemistry.

[31]  X. Wan,et al.  Cross coupling of acyl and aminyl radicals: direct synthesis of amides catalyzed by Bu4NI with TBHP as an oxidant. , 2012, Angewandte Chemie.

[32]  G. Chelucci.  Synthesis and metal-catalyzed reactions of gem-dihalovinyl systems. , 2012, Chemical reviews.

[33]  M. Greaney,et al.  Oxidative C-H homodimerization of phenylacetamides. , 2011, Organic letters.

[34]  N. Santos,et al.  Peptide drug discovery and development : translational research in academia and industry , 2011 .

[35]  Lei Wang,et al.  Direct amidation of azoles with formamides via metal-free C-H activation in the presence of tert-butyl perbenzoate. , 2011, Chemical communications.

[36]  B. Bhanage,et al.  Palladium-catalyzed carbon-monoxide-free aminocarbonylation of aryl halides using N-substituted formamides as an amide source. , 2011, The Journal of organic chemistry.

[37]  G. Lai,et al.  Utility of Dysprosium as a Reductant in Coupling Reactions of Acyl Chlorides: The Synthesis of Amides and Diaryl-Substituted Acetylenes , 2011 .

[38]  Nuno C. Santos,et al.  Comprar Peptide Drug Discovery And Development: Translational Research In Academia And Industry | Miguel Castanho | 9783527328918 | Wiley , 2011 .

[39]  J. Ichikawa,et al.  Transition-metal-catalyzed Electrophilic Activation of 1,1-Difluoro-1-alkenes : Oxindole Synthesis via Intramolecular Amination , 2010 .

[40]  J. Terao,et al.  Palladium-catalyzed intermolecular addition of formamides to alkynes. , 2010, Journal of the American Chemical Society.

[41]  J. Muzart.  N,N-Dimethylformamide: much more than a solvent , 2009 .

[42]  Bin Xu,et al.  Palladium-catalyzed amidation-hydrolysis reaction of gem-dihaloolefins: efficient synthesis of homologated carboxamides from ketones. , 2009, Chemical communications.

[43]  M. Bradley,et al.  Amide bond formation: beyond the myth of coupling reagents. , 2009, Chemical Society reviews.

[44]  Bo Yang,et al.  Synthesis, Cytotoxicity and Protein Kinase C Inhibition of Arylpyrrolylmaleimides , 2008, Archiv der Pharmazie.

[45]  E. V. D. Eycken,et al.  A convenient microwave-assisted desulfitative dimethylamination of the 2(1H)-pyrazinone scaffold using N,N-dimethylformamide , 2008 .

[46]  J. Moon,et al.  Aminocarbonylation of aryl halides using a nickel phosphite catalytic system. , 2007, Organic letters.

[47]  S. Sano,et al.  Development of a novel fungicide, cyflufenamid , 2007 .

[48]  Justyna B. Walkowiak,et al.  1,1,3,3,3-Pentafluoropropene secondary amine adducts new selective fluorinating agents , 2006 .

[49]  J. Hartwig,et al.  Palladium-Catalyzed Intermolecular α-Arylation of Zinc Amide Enolates under Mild Conditions , 2006 .

[50]  K. Uneyama,et al.  A novel route to dipeptides via noncondensation of amino acids: 2-aminoperfluoropropene as a synthon for trifluoroalanine dipeptides. , 2006, Organic letters.

[51]  C. Montalbetti,et al.  Amide bond formation and peptide coupling , 2005 .

[52]  R. Pandey,et al.  Palladium-catalyzed conversion of benzylic and allylic halides into α-aryl and β,γ-unsaturated tertiary amides by the use of a carbamoylsilane , 2005 .

[53]  A. Agarwal,et al.  Convenient Dimethylamino Amination in Heterocycles and Aromatics with Dimethylformamide , 2004 .

[54]  M. Deng,et al.  Palladium-catalyzed synthesis of arylacetamides from arylboronic acids , 2003 .

[55]  C. Xue,et al.  Palladium-catalyzed cross-coupling reaction of aryldioxaborolane with 2-bromo-N,N-dimethylacetamide , 2003 .

[56]  C. Breneman,et al.  The amide linkage : structural significance in chemistry, biochemistry, and materials science , 2003 .

[57]  Young Gyu Kim,et al.  An efficient method for one-carbon elongation of aryl aldehydes via their dibromoalkene derivatives , 2002 .

[58]  T. Hiyama,et al.  Carbon monoxide free aminocarbonylation of aryl and alkenyl iodides using DMF as an amide source. , 2002, Organic letters.

[59]  W. Shen,et al.  A facile one-carbon homologation of aryl aldehydes to amides. , 2002, Organic letters.

[60]  C. Bataille,et al.  C-H insertion approach to the synthesis of endo,exo-furofuranones: synthesis of (+/-)-asarinin, (+/-)-epimagnolin A, and (+/-)-fargesin. , 2001, The Journal of organic chemistry.

[61]  A. Ghose,et al.  A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. , 1999, Journal of combinatorial chemistry.

[62]  A. Chamberlin,et al.  Chemical Synthesis of Natural Product Peptides: Coupling Methods for the Incorporation of Noncoded Amino Acids into Peptides. , 1997, Chemical reviews.

[63]  T. Minami,et al.  The Reaction of 2,2-Difluorovinyl Ketones with Amines: A Facile Method for Preparation of α-Oxoketenimines and Acetoacetylation of Amines , 1996 .

[64]  J. Svoboda,et al.  Fluorinated 3-diethylaminopropenoates and their reactions , 1981 .

[65]  T. Nakai,et al.  DEFLUORINATIVE COUPLING REACTIONS OF gem-DIFLUOROOLEFINS WITH ORGANOLITHIUM REAGENTS. NOVEL, FACILE METHODS FOR CHAIN ELONGATIONS OF ALDEHYDES LEADING TO AMIDES, ACETYLENES, AND KETONES , 1980 .