AIBN-initiated metal free amidation of aldehydes using N-chloroamines

An efficient and environmentally benign amidation of aldehydes with N-chloroamines has been developed using AIBN as an initiator. This methodology offers a metal free and base free approach and is endowed with mild reaction conditions, high yields, and good functional group tolerance.

[1]  Tirumaleswararao Guntreddi,et al.  MnO2 promoted sequential C-O and C-N bond formation via C-H activation of methylarenes: a new approach to amides. , 2013, Organic letters.

[2]  Neetu Singh,et al.  An Efficient Tetrabutylammonium Fluoride (TBAF)‐Catalyzed Three‐Component Synthesis of 3‐Substituted Indole Derivatives under Solvent‐Free Conditions , 2013 .

[3]  Tirumaleswararao Guntreddi,et al.  Utilization of carbon disulfide as a powerful building block for the synthesis of 2-aminobenzoxazoles , 2013 .

[4]  Bharat Kumar Allam,et al.  A novel and simple transamidation of carboxamides in 1,4-dioxane without a catalyst , 2013 .

[5]  Jing Wang,et al.  Copper-catalyzed oxidative coupling of alkenes with aldehydes: direct access to α,β-unsaturated ketones. , 2013, Angewandte Chemie.

[6]  D. Raghuvanshi,et al.  Cooperatively assisted N-arylation using organic ionic base–Brønsted acid combination under controlled microwave heating , 2013 .

[7]  Bharat Kumar Allam,et al.  Hypervalent iodine catalyzed transamidation of carboxamides with amines , 2013 .

[8]  N. Iranpoor,et al.  Palladium-free aminocarbonylation of aryl, benzyl, and styryl iodides and bromides by amines using Mo(CO)6 and norbornadiene , 2013 .

[9]  D. Raghuvanshi,et al.  An efficient synthesis of 2H-chromen-3-yl derivatives via CuI/(NH4)2HPO4 catalyzed reaction of O-propargyl salicylaldehydes with active methylene compounds , 2013 .

[10]  M. Larhed,et al.  Aminocarbonylations employing Mo(CO)6 and a bridged two-vial system: allowing the use of nitro group substituted aryl iodides and aryl bromides. , 2012, The Journal of organic chemistry.

[11]  L. D. Luca,et al.  Iron‐Catalyzed Amidation of Aldehydes with N‐Chloroamines , 2012 .

[12]  G. Giacomelli,et al.  One-pot synthesis of amides from aldehydes and amines via C-H bond activation. , 2012, Organic letters.

[13]  Dang Thanh Tuan,et al.  Copper-catalyzed oxidative amidation of aldehydes with amine salts: synthesis of primary, secondary, and tertiary amides. , 2012, The Journal of organic chemistry.

[14]  A. Gupta,et al.  Nickel-mediated N-arylation with arylboronic acids: an avenue to Chan-Lam coupling. , 2012, Organic letters.

[15]  Mayur V. Khedkar,et al.  Oxidative Aminocarbonylation of Terminal Alkynes for the Synthesis of Alk‐2‐ynamides by Using Palladium‐on‐Carbon as Efficient, Heterogeneous, Phosphine‐Free, and Reusable Catalyst , 2012 .

[16]  Kana Yamamoto,et al.  Aerobic amide bond formation with N-hydroxysuccinimide. , 2012, Chemistry, an Asian journal.

[17]  J. Sorres,et al.  Boric acid: a highly efficient catalyst for transamidation of carboxamides with amines. , 2012, Organic letters.

[18]  M. Yus,et al.  Copper(II) acetate-catalyzed one-pot conversion of aldehydes into primary amides through a Beckmann-type rearrangement , 2012 .

[19]  C. Chai,et al.  Iron-Catalyzed Efficient Synthesis of Amides from Aldehydes and Amine Hydrochloride Salts , 2012 .

[20]  K. Mashima,et al.  Sodium methoxide: a simple but highly efficient catalyst for the direct amidation of esters. , 2012, Chemical communications.

[21]  H. Neumann,et al.  Efficient copper(II)-catalyzed transamidation of non-activated primary carboxamides and ureas with amines. , 2012, Angewandte Chemie.

[22]  Helena Lundberg,et al.  Direct amide coupling of non-activated carboxylic acids and amines catalysed by zirconium(IV) chloride. , 2012, Chemistry.

[23]  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.

[24]  D. Albanese,et al.  Cyanuric chloride catalyzed Beckmann rearrangement of ketoximes in biodegradable ionic liquids , 2012 .

[25]  C. Allen,et al.  Transamidation of primary amides with amines using hydroxylamine hydrochloride as an inorganic catalyst. , 2012, Angewandte Chemie.

[26]  Y. Chen,et al.  Ph3P/I2-Catalyzed Beckmann Rearrangement of Ketoximes into Amides , 2012 .

[27]  C. Chai,et al.  Atmospheric pressure aminocarbonylation of aryl iodides using palladium nanoparticles supported on MOF-5. , 2012, Chemical communications.

[28]  K. Shimizu,et al.  Transamidation of amides with amines under solvent-free conditions using a CeO2 catalyst , 2012 .

[29]  M. Lemaire,et al.  Oxidative nucleophilic substitution: transformation of alkylboronic derivatives , 2011 .

[30]  B. Bhanage,et al.  Carbon Monoxide‐Free One‐Step Synthesis of Isoindole‐1,3‐diones by Cycloaminocarbonylation of o‐Haloarenes Using Formamides , 2011 .

[31]  Ji Zhang,et al.  Cobalt-catalyzed benzylic C–H amination via dehydrogenative-coupling reaction , 2011 .

[32]  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.

[33]  J. Augustine,et al.  An Efficient Catalytic Method for the Beckmann Rearrangement of Ketoximes to Amides and Aldoximes to Nitriles Mediated by Propylphosphonic Anhydride (T3P , 2011 .

[34]  T. Sheppard,et al.  Borate esters as convenient reagents for direct amidation of carboxylic acids and transamidation of primary amides. , 2011, Organic & biomolecular chemistry.

[35]  Youquan Deng,et al.  Organic ligand-free alkylation of amines, carboxamides, sulfonamides, and ketones by using alcohols catalyzed by heterogeneous Ag/Mo oxides. , 2011, Chemistry.

[36]  K. Driller,et al.  A general and selective iron-catalyzed aminocarbonylation of alkynes: synthesis of acryl- and cinnamides. , 2011, Angewandte Chemie.

[37]  W. Ren,et al.  Mo(CO)(6)-mediated carbamoylation of aryl halides. , 2010, The Journal of organic chemistry.

[38]  Bryan E. Roberts,et al.  Molybdenum-mediated carbonylation of aryl halides with nucleophiles using microwave irradiation. , 2010, Organic letters.

[39]  Bo Shen,et al.  ‘Umpolung’ Reactivity in Semiaqueous Amide and Peptide Synthesis , 2010, Nature.

[40]  J. Mayer,et al.  Tuning of the thermochemical and kinetic properties of ascorbate by its local environment: solution chemistry and biochemical implications. , 2010, Journal of the American Chemical Society.

[41]  M. Zanda,et al.  A new entry of amination reagents for heteroaromatic C-H bonds: copper-catalyzed direct amination of azoles with chloroamines at room temperature. , 2010, Journal of the American Chemical Society.

[42]  S. Ghosh,et al.  Direct amide synthesis from either alcohols or aldehydes with amines: activity of Ru(II) hydride and Ru(0) complexes. , 2010, The Journal of organic chemistry.

[43]  A. Studer,et al.  Oxidative amidation and azidation of aldehydes by NHC catalysis. , 2010, Organic letters.

[44]  W. Ren,et al.  Carbamoylation of aryl halides by molybdenum or tungsten carbonyl amine complexes. , 2010, The Journal of organic chemistry.

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

[46]  K. Hashimoto,et al.  Amidation of alcohols with nitriles under solvent-free conditions using molecular iodine as a catalyst. , 2010, Journal of oleo science.

[47]  E. R. Jarvo,et al.  Umpolung amination: nickel-catalyzed coupling reactions of N,N-dialkyl-N-chloroamines with diorganozinc reagents. , 2009, Journal of the American Chemical Society.

[48]  H. Neumann,et al.  Palladium‐Catalyzed Carbonylation Reactions of Alkenes and Alkynes , 2009 .

[49]  S. Gellman,et al.  Catalytic transamidation reactions compatible with tertiary amide metathesis under ambient conditions. , 2009, Journal of the American Chemical Society.

[50]  J. Choe,et al.  The scope and limitation of nickel-catalyzed aminocarbonylation of aryl bromides from formamide derivatives. , 2009, The Journal of organic chemistry.

[51]  Fan Xu,et al.  Anionic Bridged Bis(amidinate) Lithium Lanthanide Complexes: Efficient Bimetallic Catalysts for Mild Amidation of Aldehydes with Amines , 2009 .

[52]  S. Minakata.  Utilization of N-X bonds in the synthesis of N-heterocycles. , 2009, Accounts of chemical research.

[53]  H. Neumann,et al.  Palladium-catalyzed carbonylation reactions of aryl halides and related compounds. , 2009, Angewandte Chemie.

[54]  Cunwei Qian,et al.  Trisguanidinate Lanthanide Complexes: Syntheses, Structures, and Catalytic Activity for Mild Amidation of Aldehydes with Amines , 2009 .

[55]  R. Madsen,et al.  Amide synthesis from alcohols and amines by the extrusion of dihydrogen. , 2008, Journal of the American Chemical Society.

[56]  P. Hanson,et al.  Domino Heck-Aza-Michael Reactions: A One-Pot, Sequential Three-Component Approach to 1,1-Dioxido-1,2-benzisothiazoline-3-acetic Acid. , 2008, European journal of organic chemistry.

[57]  Yuyang Jiang,et al.  Efficient intermolecular iron-catalyzed amidation of C-H bonds in the presence of N-bromosuccinimide. , 2008, Organic letters.

[58]  J. Chang,et al.  Highly efficient ruthenium(II) porphyrin catalyzed amidation of aldehydes. , 2008, Angewandte Chemie.

[59]  T. Marks,et al.  Mild amidation of aldehydes with amines mediated by lanthanide catalysts. , 2008, Organic letters.

[60]  Q. Cui,et al.  Discovery and mechanistic study of Al(III)-catalyzed transamidation of tertiary amides. , 2008, Journal of the American Chemical Society.

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

[62]  C. Wolf,et al.  Metal-free one-pot oxidative amination of aldehydes to amides. , 2007, Organic letters.

[63]  C. Ramalingan,et al.  Mercury-catalyzed rearrangement of ketoximes into amides and lactams in acetonitrile. , 2007, The Journal of organic chemistry.

[64]  John D. Hayler,et al.  Key green chemistry research areas—a perspective from pharmaceutical manufacturers , 2007 .

[65]  M. Kunishima,et al.  Immobilized triazine-type dehydrocondensing reagents for carboxamide formation: ROMP-Trz-Cl and ROMP(OH)-Trz-Cl. , 2007, Chemical & pharmaceutical bulletin.

[66]  V. Savić,et al.  Stereoselective synthesis of N-alkylaziridines from N-chloroamines. , 2006, Chemical Communications.

[67]  Chao‐Jun Li,et al.  Highly efficient oxidative amidation of aldehydes with amine hydrochloride salts. , 2006, Journal of the American Chemical Society.

[68]  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 .

[69]  B. Maity,et al.  Direct carbamoylation of alkenyl halides. , 2002, Organic letters.

[70]  Y. Wan,et al.  Dimethylformamide as a carbon monoxide source in fast palladium-catalyzed aminocarbonylations of aryl bromides. , 2002, The Journal of organic chemistry.

[71]  M. Beller,et al.  Catalytic Amination of Aldehydes to Amides , 2001 .

[72]  Martinez-Barrasa,et al.  Synthesis of biaryls via intermolecular radical addition of heteroaryl and aryl bromides onto arenes , 2000, Organic letters.

[73]  D. Clive,et al.  Synthesis of biaryls by intramolecular radical transfer: use of phosphinates , 2000 .

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

[75]  H. Heaney,et al.  Oxidation during reductive cyclisations using Bu3SnH , 1991 .

[76]  P. Kovacic,et al.  Chemistry of N-bromamines and N-chloramines , 1970 .

[77]  P. G. Gassman,et al.  Chemistry of nitrenium ions. X. Solvolysis of 1-chloroaziridines , 1970 .

[78]  G. H. Coleman.  The Reaction of Alkylchloroamines with Grignard Reagents , 1933 .