A Convenient and Efficient Palladium‐Catalyzed Carbonylative Sonogashira Transformation with Formic Acid as the CO Source

A practical, convenient, and efficient palladium-catalyzed carbonylative Sonogashira reaction of aryl iodides was developed. With formic acid as the CO source and dicyclohexylcarbodiimide as the activator, various alkynones were produced in good to excellent yields.

[1]  Dong-Su Kim,et al.  Synthesis of Amides and Phthalimides via a Palladium Catalyzed Aminocarbonylation of Aryl Halides with Formic Acid and Carbodiimides. , 2016, Chemistry, an Asian journal.

[2]  Xiao‐Feng Wu,et al.  Recent Achievements in Carbonylation Reactions: A Personal Account , 2016, Synlett.

[3]  Yian Shi,et al.  An Effective Pd-Catalyzed Regioselective Hydroformylation of Olefins with Formic Acid. , 2016, Journal of the American Chemical Society.

[4]  Xiao‐Feng Wu,et al.  A Convenient Palladium-Catalyzed Carbonylative Synthesis of Benzofuran-2(3 H)-ones with Formic Acid as the CO Source. , 2016, Chemistry, an Asian journal.

[5]  Xiao‐Feng Wu,et al.  Benzene-1,3,5-triyl triformate (TFBen): a convenient, efficient, and non-reacting CO source in carbonylation reactions , 2016 .

[6]  Xiao‐Feng Wu,et al.  Selective palladium-catalyzed carbonylative synthesis of aurones with formic acid as the CO source , 2016 .

[7]  Xiao‐Feng Wu,et al.  Palladium‐Catalyzed Oxidative Carbonylation of Aromatic C−H Bonds with Alcohols using Molybdenum Hexacarbonyl as the Carbon Monoxide Source , 2016 .

[8]  Xiao‐Feng Wu,et al.  Palladium‐Catalyzed Carbonylative Synthesis of Aryl Formates under Mild Conditions , 2016 .

[9]  Xiao‐Feng Wu,et al.  Palladium-catalyzed alkoxycarbonylation of aryl halides with phenols employing formic acid as the CO source , 2016 .

[10]  Xiao‐Feng Wu,et al.  A Convenient Palladium-Catalyzed Reductive Carbonylation of Aryl Iodides with Dual Role of Formic Acid. , 2016, Chemistry.

[11]  Xiao‐Feng Wu,et al.  A Convenient Palladium-Catalyzed Carbonylative Suzuki Coupling of Aryl Halides with Formic Acid as the Carbon Monoxide Source. , 2015, Chemistry.

[12]  Peter Koóš,et al.  Zn-Mediated Reduction of Oxalyl Chloride Forming CO and Its Application in Carbonylation Reactions. , 2015, Organic letters.

[13]  Xiao‐Feng Wu,et al.  Palladium-Catalyzed Carbonylative Cyclization of Arenes by C-H Bond Activation with DMF as the Carbonyl Source. , 2015, Chemistry.

[14]  Xiao‐Feng Wu,et al.  Palladium-Catalyzed One-Pot Carbonylative Sonogashira Reaction Employing Formic acid as the CO Source. , 2015, Chemistry, an Asian journal.

[15]  P. Langer,et al.  Palladium-Catalyzed Carbonylative Synthesis of N-Benzoylindoles with Mo(CO)6 as the Carbon Monoxide Source , 2015 .

[16]  T. Ulven,et al.  Oxalyl chloride as a practical carbon monoxide source for carbonylation reactions. , 2015, Organic letters.

[17]  Qi‐Lin Zhou,et al.  Palladium-catalyzed hydrocarboxylation of alkynes with formic acid. , 2015, Angewandte Chemie.

[18]  Xiao‐Feng Wu,et al.  Palladium-catalyzed carbonylative Sonogashira coupling between aryl triazenes and alkynes. , 2015, Organic & biomolecular chemistry.

[19]  Matej Babjak,et al.  Iron Pentacarbonyl in Alkoxy- and Aminocarbonylation of Aromatic Halides , 2014 .

[20]  Xiao‐Feng Wu,et al.  Palladium-catalyzed carbonylative synthesis of benzoxazinones from N-(o-bromoaryl)amides using paraformaldehyde as the carbonyl source. , 2014, The Journal of organic chemistry.

[21]  H. Neumann,et al.  Palladium-catalyzed carbonylations of aryl bromides using paraformaldehyde: synthesis of aldehydes and esters. , 2014, Angewandte Chemie.

[22]  H. Neumann,et al.  Palladium-catalyzed oxidative carbonylative coupling of arylboronic acids with terminal alkynes to alkynones. , 2014, Organic & biomolecular chemistry.

[23]  B. Bang-Andersen,et al.  Palladium-catalyzed carbonylative sonogashira coupling of aryl bromides using near stoichiometric carbon monoxide. , 2014, Organic letters.

[24]  Matej Babjak,et al.  Homogeneous Cyclocarbonylation of Alkenols with Iron Pentacarbonyl , 2014 .

[25]  Xiuling Cui,et al.  "One pot" regiospecific synthesis of polysubstituted pyrroles from benzylamines and ynones under metal free conditions. , 2013, Chemical communications.

[26]  Sunwoo Lee,et al.  Pd-catalyzed selective carbonylative and non-carbonylative couplings of propiolic acid: one-pot synthesis of diarylalkynones. , 2013, Organic letters.

[27]  T. Skrydstrup,et al.  Effective palladium-catalyzed hydroxycarbonylation of aryl halides with substoichiometric carbon monoxide. , 2013, Journal of the American Chemical Society.

[28]  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.

[29]  J. P. Harrity,et al.  Synthesis of ynone trifluoroborates toward functionalized pyrazoles. , 2012, Organic letters.

[30]  M. Sonoda,et al.  Pd-catalyzed coupling reaction of acid chlorides with terminal alkynes using 1-(2-pyridylethynyl)-2-(2-thienylethynyl)benzene ligand , 2012 .

[31]  Lei Chen,et al.  Synthesis of trisubstituted isoxazoles by palladium(II)-catalyzed cascade cyclization-alkenylation of 2-alkyn-1-one O-methyl oximes. , 2012, The Journal of organic chemistry.

[32]  M. Larhed,et al.  Molybdenum Hexacarbonyl MediatedCO Gas-Free Carbonylative Reactions , 2012 .

[33]  K. Parthasarathy,et al.  Iron‐Catalyzed Synthesis of β‐Chlorovinyl and α,β‐Alkynyl Ketones from Terminal and Silylated Alkynes with Acid Chlorides , 2012 .

[34]  H. Neumann,et al.  Convenient and general palladium-catalyzed carbonylative Sonogashira coupling of aryl amines. , 2011, Angewandte Chemie.

[35]  H. Neumann,et al.  Palladium-catalyzed carbonylative coupling of benzyl chlorides with terminal alkynes to give 1,4-diaryl-3-butyn-2-ones and related furanones. , 2011, Organic & biomolecular chemistry.

[36]  R. Fröhlich,et al.  Reaktionen frustrierter Lewis‐Paare mit konjugierten Inonen – selektive Hydrierung der Kohlenstoff‐Kohlenstoff‐Dreifachbindung , 2011 .

[37]  R. Fröhlich,et al.  Reaction of frustrated Lewis pairs with conjugated ynones-selective hydrogenation of the carbon-carbon triple bond. , 2011, Angewandte Chemie.

[38]  H. Neumann,et al.  A general cyclocarbonylation of aryl bromides and triflates with acetylenes: palladium-catalyzed synthesis of 3-alkylidenefuran-2-ones. , 2011, Chemistry.

[39]  M. Larhed,et al.  Microwave-assisted synthesis of Weinreb and MAP aryl amides via Pd-catalyzed Heck aminocarbonylation using Mo(CO)6 or W(CO)6. , 2011, The Journal of organic chemistry.

[40]  P. Bera,et al.  A supported palladium nanocatalyst for copper free acyl Sonogashira reactions: One-pot multicomponent synthesis of N-containing heterocycles , 2011 .

[41]  H. Neumann,et al.  A general palladium-catalyzed carbonylative sonogashira coupling of aryl triflates. , 2011, Chemistry.

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

[43]  H. Neumann,et al.  A general and convenient palladium-catalyzed carbonylative Sonogashira coupling of aryl bromides. , 2010, Chemistry.

[44]  M. L. Rao,et al.  Oxalyl chloride as carbonyl synthon in Pd-catalyzed carbonylations of triarylbismuth and triarylindium organometallic nucleophiles , 2010 .

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

[46]  T. Fukuyama,et al.  Synthesis of alkyl alkynyl ketones by Pd/light-induced three-component coupling reactions of iodoalkanes, CO, and 1-alkynes. , 2010, Organic letters.

[47]  A. Capretta,et al.  Access to flavones via a microwave-assisted, one-pot Sonogashira-carbonylation-annulation reaction. , 2009, Organic letters.

[48]  A. Valleix,et al.  Flexible synthesis of pyrimidines with chiral monofluorinated and difluoromethyl side chains. , 2009, The Journal of organic chemistry.

[49]  K. Kakiuchi,et al.  Rh(I)-catalyzed CO gas-free carbonylative cyclization reactions of alkynes with 2-bromophenylboronic acids using formaldehyde. , 2009, Organic letters.

[50]  M. Larhed,et al.  Microwave-promoted aminocarbonylation of aryl triflates using Mo(CO)6 as a solid CO source , 2008 .

[51]  T. Müller,et al.  Catalytic alkynone generation by Sonogashira reaction and its application in three-component pyrimidine synthesis , 2008, Nature Protocols.

[52]  Wei Sun,et al.  Magnetically separable Pd catalyst for carbonylative Sonogashira coupling reactions for the synthesis of alpha,beta-alkynyl ketones. , 2008, Organic letters.

[53]  Huanfeng Jiang,et al.  One‐Pot Three‐Component Synthesis of Pyrazoles Through a Tandem Coupling‐Cyclocondensation Sequence. , 2008 .

[54]  M. Aschi,et al.  Pd-catalyzed regioselective hydroarylation of α-(2-aminoaryl)-α,β-ynones with organoboron derivatives as a tool for the synthesis of quinolines: experimental evidence and quantum-chemical calculations , 2008 .

[55]  J. Chen,et al.  A simple and efficient recyclable phosphine-free catalytic system for alkoxycarbonylation and carbonylative Sonogashira coupling reactions of aryl iodides , 2008 .

[56]  H. Laatsch,et al.  Isolation, Enantioselective Total Synthesis and Structure Determination of the Anthrapyran Metabolite SS 43405‐e , 2007 .

[57]  Kiev S. Ly,et al.  Microwave assisted, palladium catalyzed aminocarbonylations of heteroaromatic bromides using solid Mo(CO)6 as the carbon monoxide source , 2007 .

[58]  M. Sandvik,et al.  Antibodies with broad specificity to azaspiracids by use of synthetic haptens. , 2006, Journal of the American Chemical Society.

[59]  K. Srinivasan,et al.  Copper-, ligand- and solvent-free synthesis of ynones by coupling acid chlorides with terminal alkynes , 2006 .

[60]  Victor Sans,et al.  PdCl2(P(OPh)3)2 Catalyzed Coupling and Carbonylative Coupling of Phenylacetylenes with Aryl Iodides in Organic Solvents and in Ionic Liquids , 2006 .

[61]  Masaaki Sato,et al.  Low pressure Pd-catalyzed carbonylation in an ionic liquid using a multiphase microflow system. , 2006, Chemical communications.

[62]  M. Larhed,et al.  Microwave-promoted aminocarbonylations of aryl chlorides using Mo(CO)(6) as a solid carbon monoxide source. , 2006, Journal of combinatorial chemistry.

[63]  Alexei S. Karpov,et al.  Kurze Meridianin‐Synthesen durch carbonylierende Alkinylierung; eine Vierkomponenten‐Pyrimidin‐Synthese , 2005 .

[64]  F. Rominger,et al.  Concise syntheses of meridianins by carbonylative alkynylation and a four-component pyrimidine synthesis. , 2005, Angewandte Chemie.

[65]  Jae Nyoung Kim,et al.  Facile synthesis of α,β-acetylenic ketones and 2,5-disubstituted furans : consecutive activation of triple and double bond with ZnBr2 toward the synthesis of furan ring , 2005 .

[66]  A. Mori,et al.  One-pot construction of pyrazoles and isoxazoles with palladium-catalyzed four-component coupling. , 2005, Organic letters.

[67]  Baomin Wang,et al.  A straightforward synthesis of ynones by reaction of dimethylalkynylaluminum reagents with acid chlorides. , 2005, The Journal of organic chemistry.

[68]  Zhen Yang,et al.  Pd-catalyzed copper-free carbonylative Sonogashira reaction of aryl iodides with alkynes for the synthesis of alkynyl ketones and flavones by using water as a solvent. , 2005, The Journal of organic chemistry.

[69]  T. Fukuyama,et al.  Synthesis of acetylenic ketones by a Pd-catalyzed carbonylative three-component coupling reaction in [bmim]PF6 , 2005 .

[70]  Chao‐Jun Li,et al.  A remarkably efficient coupling of acid chlorides with alkynes in water. , 2004, Organic letters.

[71]  G. Fabrizi,et al.  Palladium-catalyzed synthesis of aldehydes from aryl iodides and acetic formic anhydride. , 2004, Journal of combinatorial chemistry.

[72]  C. Nájera,et al.  Synthesis of ynones by palladium-catalyzed acylation of terminal alkynes with acid chlorides. , 2004, The Journal of organic chemistry.

[73]  G. Fabrizi,et al.  Palladium-catalyzed hydroxycarbonylation of aryl and vinyl halides or triflates by acetic anhydride and formate anions. , 2003, Organic letters.

[74]  A. Mori,et al.  Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia. , 2003, Organic letters.

[75]  Sukbok Chang,et al.  Ru-catalyzed hydroamidation of alkenes and cooperative aminocarboxylation procedure with chelating formamide. , 2003, Organic letters.

[76]  A. Hallberg,et al.  Rapid palladium-catalyzed synthesis of esters from aryl halides utilizing Mo(CO)(6) as a solid carbon monoxide source. , 2003, Journal of combinatorial chemistry.

[77]  M. Larhed,et al.  Increasing rates and scope of reactions: sluggish amines in microwave-heated aminocarbonylation reactions under air. , 2003, The Journal of organic chemistry.

[78]  Chongmok Lee,et al.  Chelation-accelerated sequential decarbonylation of formate and alkoxycarbonylation of aryl halides using a combined Ru and Pd catalyst. , 2003, The Journal of organic chemistry.

[79]  C. Meyer,et al.  New flexible synthesis of pyrazoles with different, functionalized substituents at C3 and C5. , 2002, The Journal of organic chemistry.

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

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

[82]  J. Marco-Contelles,et al.  Synthesis of Enantiomerically Pure, Highly Functionalized, Medium-Sized Carbocycles from Carbohydrates: Formal Total Synthesis of (+)-Calystegine B2 , 2002 .

[83]  K. Takagi,et al.  Catalytic Pauson-Khand-type reaction using aldehydes as a CO source. , 2002, Organic letters.

[84]  K. Kakiuchi,et al.  CO-transfer carbonylation reactions. A catalytic Pauson-Khand-type reaction of enynes with aldehydes as a source of carbon monoxide. , 2002, Journal of the American Chemical Society.

[85]  A. Hallberg,et al.  In situ generation of carbon monoxide from solid molybdenum hexacarbonyl. A convenient and fast route to palladium-catalyzed carbonylation reactions. , 2002, Journal of combinatorial chemistry.

[86]  A. Kel'in,et al.  A novel Cu-assisted cycloisomerization of alkynyl imines: efficient synthesis of pyrroles and pyrrole-containing heterocycles. , 2001, Journal of the American Chemical Society.

[87]  T. Tsuchiya,et al.  Palladium-catalyzed cross-coupling reactions between 1-alkynylstibines and acyl chlorides , 2000 .

[88]  Suk-Ku Kang,et al.  Synthesis of Alkynyl Ketones via Palladium- and Copper-Catalyzed Carbonylative Cross Coupling of Iodonium Salts with Alk-1-ynes , 1997 .

[89]  P. Pace,et al.  The Palladium-Catalysed Carbonylative Coupling of 5-(Trimethylsilylethynyl)-3’,5’-di-O-acetyl-2’-deoxyuridine and 1-Alkynes with Aryl Iodides , 1995 .

[90]  H. Alper,et al.  Coupling and Carbonylation of Iodoaromatics and Terminal Alkynes or Alkynols Catalyzed by a Dimeric Palladium Hydroxide , 1994 .

[91]  Toshi-aki Kobayashi,et al.  Carbonylation of organic halides in the presence of terminal acetylenes; novel acetylenic ketone synthesis , 1981 .

[92]  Y. Tohda,et al.  A Convenient Synthesis of 1-Alkynyl Ketones and 2-Alkynamides , 1977 .