Palladium‐Catalyzed Carbonylation of Indoles using Aryl Formates as Bifunctional Reagents: A Route to Indol‐3‐yl Aryl Ketones

A new Pd‐catalyzed carbonylation of indoles for the synthesis of indol‐3‐yl aryl ketones under CO‐free conditions was developed. The reaction showed a broad substrate scope with moderate to excellent yields.

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

[2]  Gan-peng Li,et al.  Acylation of indoles via photoredox catalysis: a route to 3-acylindoles , 2016 .

[3]  Xiao‐Feng Wu,et al.  Palladium-catalyzed carbonylative C–H activation of arenes with norbornene as the coupling partner , 2016 .

[4]  Gan-peng Li,et al.  Synthesis of indol-3-yl aryl ketones through visible-light-mediated carbonylation , 2016 .

[5]  Can Li,et al.  A highly enantioselective thiolation of sulfonyl indoles to access 3-sec-sulfur-substituted indoles in water. , 2016, Chemical communications.

[6]  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.

[7]  Xiao‐Feng Wu,et al.  Pd/C-catalyzed carbonylative C–H activation with DMF as the CO source , 2015 .

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

[9]  S. Ji,et al.  Palladium-Catalyzed Carbonylative Annulation Reactions Using Aryl Formate as a CO Source: Synthesis of 2-Substituted Indene-1,3(2H)-dione Derivatives. , 2015, The Journal of organic chemistry.

[10]  B. Bhanage,et al.  Recent advances in the transition metal catalyzed carbonylation of alkynes, arenes and aryl halides using CO surrogates , 2015 .

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

[12]  Xiao‐Feng Wu Acylation of (Hetero)Arenes through C-H Activation with Aroyl Surrogates. , 2015, Chemistry.

[13]  Lijun Gu,et al.  Metal-free, visible-light-mediated transformation of aryl diazonium salts and (hetero)arenes: an efficient route to aryl ketones , 2015 .

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

[15]  B. Bhanage,et al.  Carbonylative Synthesis of Phthalimides and Benzoxazinones by Using Phenyl Formate as a Carbon Monoxide Source , 2015 .

[16]  A. Lei,et al.  From anilines to isatins: oxidative palladium-catalyzed double carbonylation of C-H bonds. , 2015, Angewandte Chemie.

[17]  Mi-Na Zhao,et al.  Palladium-Catalyzed Carbonylation of Indoles for Synthesis of Indol-3-yl Aryl Ketones , 2015 .

[18]  H. Johansson,et al.  A Scalable Method for Regioselective 3-Acylation of 2-Substituted Indoles under Basic Conditions. , 2015, The Journal of organic chemistry.

[19]  S. H. Siddiki,et al.  Selective N-alkylation of indoles with primary alcohols using a Pt/HBEA catalyst , 2015 .

[20]  M. Ohashi,et al.  Nickel(0)-catalyzed [2 + 2 + 1] carbonylative cycloaddition of imines and alkynes or norbornene leading to γ-lactams. , 2014, Journal of the American Chemical Society.

[21]  I. Nicholls,et al.  Rhodium(III)-catalysed aerobic synthesis of highly functionalized indoles from N-arylurea under mild conditions through C-H activation. , 2014, Chemical communications.

[22]  Lijin Xu,et al.  Inside Cover: Rhodium‐Catalyzed Decarbonylative Direct C2‐Arylation of Indoles with Aryl Carboxylic Acids (ChemCatChem 11/2014) , 2014 .

[23]  N. Mishra,et al.  Decarboxylative acylation of indolines with α-keto acids under palladium catalysis: a facile strategy for the synthesis of 7-substituted indoles. , 2014, Chemical communications.

[24]  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.

[25]  M. Beller,et al.  Palladium-Catalyzed Carbonylative Transformation of C(sp3)–X Bonds , 2014 .

[26]  A. Taheri,et al.  Brønsted acid ionic liquid catalyzed facile synthesis of 3-vinylindoles through direct C3 alkenylation of indoles with simple ketones , 2014 .

[27]  M. Beller,et al.  Carbonylierungen von Alkenen mit CO‐Alternativen , 2014 .

[28]  M. Beller,et al.  Carbonylations of alkenes with CO surrogates. , 2014, Angewandte Chemie.

[29]  Andrew McNally,et al.  Palladium-catalysed C–H activation of aliphatic amines to give strained nitrogen heterocycles , 2014, Nature.

[30]  Lei Zhou,et al.  Synthesis of 3-acylindoles by visible-light induced intramolecular oxidative cyclization of o-alkynylated N,N-dialkylamines. , 2014, Organic letters.

[31]  T. Fukuyama,et al.  Carbonylation reactions of alkyl iodides through the interplay of carbon radicals and Pd catalysts. , 2014, Accounts of chemical research.

[32]  H. Neumann,et al.  Aryl formate as bifunctional reagent: applications in palladium-catalyzed carbonylative coupling reactions using in situ generated CO. , 2014, Angewandte Chemie.

[33]  C. Che,et al.  Ruthenium porphyrin catalyzed diimination of indoles with aryl azides as the nitrene source. , 2014, Chemical communications.

[34]  H. Neumann,et al.  Transition-metal-catalyzed carbonylation reactions of olefins and alkynes: a personal account. , 2014, Accounts of chemical research.

[35]  B. Bhanage,et al.  Recent developments in palladium catalysed carbonylation reactions , 2014 .

[36]  Yian Shi,et al.  A palladium-catalyzed regioselective hydroesterification of alkenylphenols to lactones with phenyl formate as CO source. , 2014, Organic letters.

[37]  Lijun Gu,et al.  Synthesis of 3-acylindoles via decarboxylative cross-coupling reaction of free (NH) indoles with α-oxocarboxylic acids , 2014 .

[38]  K. Manabe,et al.  Palladium-catalyzed fluorocarbonylation using N-formylsaccharin as CO source: general access to carboxylic acid derivatives. , 2013, Organic letters.

[39]  K. Manabe,et al.  Palladium-catalyzed reductive carbonylation of aryl halides with N-formylsaccharin as a CO source. , 2013, Angewandte Chemie.

[40]  Xiang Wu,et al.  Transition-metal-catalyzed additions of C-H bonds to C-X (X = N, O) multiple bonds via C-H bond activation. , 2013, Organic & biomolecular chemistry.

[41]  J. Kadokawa,et al.  Ruthenium-catalyzed carbonylative C-H cyclization of 2-arylphenols: a novel synthetic route to 6H-dibenzo[b,d]pyran-6-ones. , 2013, Organic letters.

[42]  Lei Wang,et al.  Copper-promoted decarboxylative direct C3-acylation of N-substituted indoles with α-oxocarboxylic acids. , 2013, Chemical communications.

[43]  H. Neumann,et al.  Palladium-catalyzed oxidative carbonylation reactions. , 2013, ChemSusChem.

[44]  T. Jiang,et al.  Synthesis of 3-acylindoles by palladium-catalyzed acylation of free (N-H) indoles with nitriles. , 2013, Organic letters.

[45]  F. Song,et al.  Facile access to 3-acylindoles through palladium-catalyzed addition of indoles to nitriles: the one-pot synthesis of indenoindolones. , 2013, Chemistry.

[46]  H. Neumann,et al.  Synthesis of heterocycles via palladium-catalyzed carbonylations. , 2013, Chemical reviews.

[47]  B. Gabriele,et al.  Oxidative Carbonylation as a Powerful Tool for the Direct Synthesis of Carbonylated Heterocycles , 2012 .

[48]  Ming Z. Chen,et al.  Palladium-catalyzed regioselective carbonylation of C-H bonds of N-alkyl anilines for synthesis of isatoic anhydrides. , 2012, Journal of the American Chemical Society.

[49]  K. Manabe,et al.  Trichlorophenyl formate: highly reactive and easily accessible crystalline CO surrogate for palladium-catalyzed carbonylation of aryl/alkenyl halides and triflates. , 2012, Organic letters.

[50]  J. Terao,et al.  Palladium-catalyzed esterification of aryl halides using aryl formates without the use of external carbon monoxide. , 2012, Chemical communications.

[51]  T. Skrydstrup,et al.  Palladium-catalyzed N-acylation of monosubstituted ureas using near-stoichiometric carbon monoxide. , 2012, The Journal of organic chemistry.

[52]  H. Neumann,et al.  Ruthenium and Rhodium‐Catalyzed Carbonylation Reactions , 2012 .

[53]  H. Neumann,et al.  A general and efficient palladium-catalyzed alkoxycarbonylation of phenols to form esters through in situ formed aryl nonaflates. , 2012, Chemistry.

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

[55]  S. Perrone,et al.  One-Pot Ester Synthesis fromAllyl and Benzyl Halides and Alcohols by Palladium-CatalyzedCarbonylation , 2012 .

[56]  Aiwen Lei,et al.  Oxidative Carbonylierungen: Organometallverbindungen (RM) oder Kohlenwasserstoffe (RH) als Nucleophile , 2011 .

[57]  Qiang Liu,et al.  Oxidative carbonylation reactions: organometallic compounds (R-M) or hydrocarbons (R-H) as nucleophiles. , 2011, Angewandte Chemie.

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

[59]  W. Su,et al.  Mild and selective Ru-catalyzed formylation and Fe-catalyzed acylation of free (N-H) indoles using anilines as the carbonyl source. , 2011, Journal of the American Chemical Society.

[60]  S. K. Guchhait,et al.  ZrCl4-mediated regio- and chemoselective Friedel-Crafts acylation of indole. , 2011, The Journal of organic chemistry.

[61]  T. Skrydstrup,et al.  Ex situ generation of stoichiometric and substoichiometric 12CO and 13CO and its efficient incorporation in palladium catalyzed aminocarbonylations. , 2011, Journal of the American Chemical Society.

[62]  E. Novellino,et al.  New arylthioindoles and related bioisosteres at the sulfur bridging group. 4. Synthesis, tubulin polymerization, cell growth inhibition, and molecular modeling studies. , 2009, Journal of medicinal chemistry.

[63]  H. Reissig,et al.  Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal-Catalyzed Reactions , 2009 .

[64]  M. Beller,et al.  Palladiumkatalysierte Carbonylierungen von Arylhalogeniden und ähnlichen Substraten , 2009 .

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

[66]  jin-quan yu,et al.  Synthesis of 1,2- and 1,3-dicarboxylic acids via Pd(II)-catalyzed carboxylation of aryl and vinyl C-H bonds. , 2008, Journal of the American Chemical Society.

[67]  M. Martinelli,et al.  C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents. , 2007, Chemical reviews.

[68]  Tsumoru Morimoto,et al.  Katalytische Carbonylierungen: kein Bedarf an Kohlenmonoxid , 2004 .

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

[70]  V. Demopoulos,et al.  Substituted pyrrol-1-ylacetic acids that combine aldose reductase enzyme inhibitory activity and ability to prevent the nonenzymatic irreversible modification of proteins from monosaccharides. , 2003, Journal of Medicinal Chemistry.

[71]  M. Faul,et al.  Palladium-catalyzed acylation of a 1,2-disubstituted 3-indolylzinc chloride , 1997 .

[72]  J. Tyman Synthetic and natural phenols , 1996 .

[73]  C. Amatore,et al.  Evidence of the formation of zerovalent palladium from Pd(OAc)2 and triphenylphosphine , 1992 .