Palladium-Catalyzed Ylidyl-Carbonylation of Aryl Halides To Produce α-Acylphosphoranes.

An efficient synthesis of α-acylphosphoranes by palladium-catalyzed carbonylation of aryl iodides with carbon monoxide and stabilized phosphonium ylides has been developed. Featuring 44 examples, the protocol displayed a wide substrate scope under mild reaction conditions, showcasing its potential in synthetic organic chemistry.

[1]  B. Bhanage,et al.  Palladium-Catalyzed Oxidative N-Dealkylation/Carbonylation of Tertiary Amines with Alkynes to α,β-Alkynylamides. , 2016, The Journal of organic chemistry.

[2]  B. Bhanage,et al.  Pd/C-Catalyzed Aminocarbonylation of Aryl Iodides via Oxidative C-N Bond Activation of Tertiary Amines to Tertiary Amides. , 2016, The Journal of organic chemistry.

[3]  I. Ryu,et al.  Palladium-catalyzed carbonylative couplings of vinylogous enolates: application to statin structures. , 2015, Journal of the American Chemical Society.

[4]  B. Bhanage,et al.  Palladacycle-Catalyzed Carbonylative Suzuki-Miyaura Coupling with High Turnover Number and Turnover Frequency. , 2015, The Journal of organic chemistry.

[5]  Jianliang Xiao,et al.  Carbonylative coupling of allylic acetates with aryl boronic acids. , 2015, Chemical communications.

[6]  W. Birchmeier,et al.  Selective Inhibitors of the Protein Tyrosine Phosphatase SHP2 Block Cellular Motility and Growth of Cancer Cells in vitro and in vivo , 2015, ChemMedChem.

[7]  T. Skrydstrup,et al.  Synthesis of acyl carbamates via four component Pd-catalyzed carbonylative coupling of aryl halides, potassium cyanate, and alcohols. , 2015, Organic letters.

[8]  J. Caravella,et al.  Novel heterocyclic scaffolds of GW4064 as farnesoid X receptor agonists. , 2015, Bioorganic & medicinal chemistry letters.

[9]  T. Skrydstrup,et al.  Palladium-catalyzed carbonylative α-arylation of 2-oxindoles with (hetero)aryl bromides: efficient and complementary approach to 3-acyl-2-oxindoles. , 2014, Angewandte Chemie.

[10]  Jianliang Xiao,et al.  Pd-catalyzed carbonylation for the construction of tertiary and quaternary carbon centers with sp(3) carbon partners. , 2014, Organic & biomolecular chemistry.

[11]  R. Manikandan,et al.  Ruthenium-catalyzed dimerization of propiolates: a simple route to α-pyrones. , 2014, Organic letters.

[12]  Yong Wang,et al.  Catalytic allylation of stabilized phosphonium ylides with primary allylic amines. , 2013, The Journal of organic chemistry.

[13]  Satish Koppireddi,et al.  Demonic axe-like conjugated alkynes in combating microbes. , 2013, European journal of medicinal chemistry.

[14]  T. Skrydstrup,et al.  Palladium-catalyzed carbonylative α-arylation for accessing 1,3-diketones. , 2012, Angewandte Chemie.

[15]  Jianliang Xiao,et al.  Carboxylic acid anhydrides via Pd-catalyzed carbonylation of aryl halides at atmospheric CO pressure. , 2012, Chemical communications.

[16]  H. Neumann,et al.  Palladium-catalyzed carbonylative coupling reactions between Ar-X and carbon nucleophiles. , 2011, Chemical Society reviews.

[17]  H. Neumann,et al.  Development of a general palladium-catalyzed carbonylative Heck reaction of aryl halides. , 2010, Journal of the American Chemical Society.

[18]  S. You,et al.  A one-pot palladium-catalyzed allylic alkylation and Wittig reaction of phosphorus ylides. , 2010, Chemistry.

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

[20]  Jörg Rademann,et al.  Specific inhibitors of the protein tyrosine phosphatase Shp2 identified by high-throughput docking , 2008, Proceedings of the National Academy of Sciences.

[21]  Ying‐Chun Chen,et al.  Organocatalytic enantioselective Mannich-type reaction of phosphorus ylides: synthesis of chiral N-boc-beta-amino-alpha-methylene carboxylic esters. , 2008, Journal of the American Chemical Society.

[22]  S. Buchwald,et al.  Palladium-catalyzed aminocarbonylation of aryl chlorides at atmospheric pressure: the dual role of sodium phenoxide. , 2007, Angewandte Chemie.

[23]  L. Kollár,et al.  Facile synthesis of primary amides and ketoamides via a palladium-catalysed carbonylation–deprotection reaction sequence , 2007 .

[24]  J. Caille,et al.  Palladium-Catalyzed Hydroxycarbonylation of Aryl and Vinyl Bromides by Mixed Acetic Formic Anhydride , 2006 .

[25]  M. Neuburger,et al.  Ethylene oligomerisation and polymerisation with nickel phosphanylenolates bearing electron-withdrawing substituents: Structure-reactivity relationships. , 2006, Chemistry.

[26]  K. Rossen,et al.  A general and efficient method for the formylation of aryl and heteroaryl bromides. , 2005, Angewandte Chemie.

[27]  J. A. Paixão,et al.  Novel Asymmetric Wittig Reaction: Synthesis of Chiral Allenic Esters , 2004 .

[28]  I. Chessell,et al.  Identification of 2,3-diaryl-pyrazolo[1,5-b]pyridazines as potent and selective cyclooxygenase-2 inhibitors. , 2004, Bioorganic & medicinal chemistry letters.

[29]  K. Kakiuchi,et al.  Evolution of carbonylation catalysis: no need for carbon monoxide. , 2004, Angewandte Chemie.

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

[31]  A. Gonsalves,et al.  Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates , 2003 .

[32]  M. Beller,et al.  Development of new palladium catalysts for the alkoxycarbonylation of aryl chlorides , 2002 .

[33]  A. Schnyder,et al.  Synthesis of unsymmetrical aroyl acyl imides by aminocarbonylation of aryl bromides. , 2002, The Journal of organic chemistry.

[34]  M. Beller,et al.  A More Efficient Catalyst for the Carbonylation of Chloroarenes. , 2001, Angewandte Chemie.

[35]  A. Gonsalves,et al.  Synthesis of 2-halo-2H-azirines , 2001 .

[36]  M. Botfield,et al.  Selective inhibition of Src SH2 by a novel thiol-targeting tricarbonyl-modified inhibitor and mechanistic analysis by (1)H/(13)C NMR spectroscopy. , 2001, Bioorganic & medicinal chemistry letters.

[37]  Kieseung Lee,et al.  A practical procedure for the selective oxidation of phosphorus keto ylides to vicinal tricarbonyls using moist magnesium monoperoxyphthalate (MMPP) in dichloromethane at ambient temperature , 2001 .

[38]  H. Alper,et al.  Palladium-Catalyzed Cyclocarbonylation of o-Iodophenols and 2-Hydroxy-3-iodopyridine with Heterocumulenes: Regioselective Synthesis of Benzo[e]-1,3-oxazin-4-one and Pyrido[3,2-e]-1,3-oxazin-4-one Derivatives , 1999 .

[39]  M. Drysdale,et al.  Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 16. Model studies for the construction of conjugated polymers , 1999 .

[40]  Takahiro Hayashi,et al.  Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones , 1998 .

[41]  H. Meshram,et al.  Zinc promoted facile method for the acylation of ylides at α-carbon , 1998 .

[42]  M. Kayser,et al.  On the synthesis and the mechanism of formation of halogenated enol lactones , 1997 .

[43]  Xian Huang,et al.  A New Synthesis of a-Acylphosphorane , 1994 .

[44]  R. Aitken,et al.  Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 2. Two-step conversion of acid chlorides into acetylenic esters and terminal alkynes , 1994 .

[45]  J. Trent,et al.  Halogenation of keto acid phosphoranes: synthesis of halo enol lactones and haloallenes , 1993 .

[46]  M. Kayser,et al.  Mechanism of Wittig reaction with cyclic anhydrides , 1992 .

[47]  R. Aitken,et al.  Convenient Two-Step Conversion of Acid Chlorides to Terminal Alkynes , 1990 .

[48]  J. Trent,et al.  A novel bromo lactonization of acylated phosphoranes. A new route to bromo enol lactones. , 1989 .

[49]  R. Amici,et al.  The chemistry of vicinal tricarbonyl compounds. Applications in the synthesis of isoquinoline alkaloids , 1989 .

[50]  H. Maeda,et al.  Reaction of Triphenylphosphine Radical Cation with 1, 3-Dicarbonyl Compounds : Electrochemical One-Step Preparation of Dioxomethylenetriphenylphosphoranes , 1988 .

[51]  J. Dunogues,et al.  Une synthese originale et inattendue d'isocoumarines fonctionnelles , 1984 .

[52]  M. P. Cooke Oxidation of acylphosphoranes with sodium hypochlorite. Substituted carboxylic acids through charge-directed conjugate addition reactions , 1983 .

[53]  J. Dunogues,et al.  Une nouvelle synthèse de dérivés de l'indanedione-1,3 , 1983 .

[54]  A. Abell,et al.  Aspects of the mechanism of the Wittig reaction between cyclic anhydrides and stabilized phosphoranes , 1982 .

[55]  M. Pétraud,et al.  Nouveau mode de cyclisation de céto-ylures.Application `a une synthèse originale d'acyl-3 hydroxy-4-coumarines et de l'hydroxy-11 benzo-(b) 12[h] xanthone-12 , 1981 .

[56]  R. Heck,et al.  Palladium-catalyzed formylation of aryl, heterocyclic, and vinylic halides , 1974 .

[57]  R. Heck,et al.  Palladium-catalyzed amidation of aryl, heterocyclic, and vinylic halides , 1974 .

[58]  R. Heck,et al.  Palladium-catalyzed carboalkoxylation of aryl, benzyl, and vinylic halides , 1974 .