Synthesis of Indoles through Domino Reactions of 2‐Fluorotoluenes and Nitriles

[1]  Jian-Ping Qu,et al.  Copper-catalyzed oxidative benzylic C-H cyclization via iminyl radical from intermolecular anion-radical redox relay , 2019, Nature Communications.

[2]  Yue Fu,et al.  Cation-π Interactions in the Benzylic Arylation of Toluenes with Bimetallic Catalysts. , 2018, Journal of the American Chemical Society.

[3]  P. Walsh,et al.  One-pot aminobenzylation of aldehydes with toluenes , 2018, Nature Communications.

[4]  Xile Hu,et al.  Cross-Coupling of Alkyl Redox-Active Esters with Benzophenone Imines: Tandem Photoredox and Copper Catalysis , 2018, Angewandte Chemie.

[5]  Xile Hu,et al.  Cross-Coupling of Alkyl Redox-Active Esters with Benzophenone Imines: Tandem Photoredox and Copper Catalysis. , 2018, Angewandte Chemie.

[6]  Xiao-Shan Ning,et al.  Pd‐tBuONO Cocatalyzed Aerobic Indole Synthesis , 2018 .

[7]  T. Colacot,et al.  Catalyst-Directed Chemoselective Double Amination of Bromo-chloro(hetero)arenes: A Synthetic Route toward Advanced Amino-aniline Intermediates. , 2018, Organic letters.

[8]  A. Mazepa,et al.  Synthesis of new hexahydro-5H-indolo[3,2-c]acridines and indolylbutanoic acids by Fischer cyclization of arylhydrazones , 2018, Chemistry of Heterocyclic Compounds.

[9]  Amos B. Smith,et al.  Total synthesis of architecturally complex indole terpenoids: strategic and tactical evolution , 2017, The Journal of Antibiotics.

[10]  D. Jacquemin,et al.  Arylazoindazole Photoswitches: Facile Synthesis and Functionalization via SNAr Substitution , 2017, Journal of the American Chemical Society.

[11]  M. Meldal,et al.  Mechanism and Scope of Base-Controlled Catalyst-Free N-Arylation of Amines with Unactivated Fluorobenzenes. , 2017, Chemistry.

[12]  J. Hartwig,et al.  Palladium-Catalyzed Cross Coupling of Secondary and Tertiary Alkyl Bromides with a Nitrogen Nucleophile , 2016, ACS central science.

[13]  A. Martı́nez-Martı́nez,et al.  Structural Studies of Cesium, Lithium/Cesium, and Sodium/Cesium Bis(trimethylsilyl)amide (HMDS) Complexes. , 2016, Inorganic chemistry.

[14]  N. Jiao,et al.  Cationic Cobalt(III) Catalyzed Indole Synthesis: The Regioselective Intermolecular Cyclization of N-Nitrosoanilines and Alkynes. , 2016, Angewandte Chemie.

[15]  F. Glorius,et al.  Cobalt(III)‐katalysierte redoxneutrale Synthese von freien Indolen durch N‐N‐Bindungsspaltung , 2016 .

[16]  F. Glorius,et al.  Cobalt(III)-Catalyzed Redox-Neutral Synthesis of Unprotected Indoles Featuring an N-N Bond Cleavage. , 2016, Angewandte Chemie.

[17]  Amitabha Sarkar,et al.  Synthesis and structure of new alkynyl derivatives of phenothiazine and phenoxazine , 2016 .

[18]  Z. Xi,et al.  Transfer of Aryl Halide to Alkyl Halide: Reductive Elimination of Alkylhalide from Alkylpalladium Halides Containing syn‐β‐Hydrogen Atoms. , 2015 .

[19]  Z. Xi,et al.  Transfer of aryl halide to alkyl halide: reductive elimination of alkylhalide from alkylpalladium halides containing syn-β-hydrogen atoms. , 2014, Angewandte Chemie.

[20]  Magnus Rueping,et al.  Synthese von Indolen mithilfe von sichtbarem Licht: Photoredoxkatalyse für die Palladium‐katalysierte C‐H‐Aktivierung , 2014 .

[21]  David C. Fabry,et al.  Synthesis of indoles using visible light: photoredox catalysis for palladium-catalyzed C-H activation. , 2014, Angewandte Chemie.

[22]  K. Scheidt,et al.  N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles. , 2014, Angewandte Chemie.

[23]  Laura Fra,et al.  Synthese von Indolen durch ein modifiziertes Koser‐Reagens , 2014 .

[24]  José A. Souto,et al.  Indole synthesis based on a modified Koser reagent. , 2014, Angewandte Chemie.

[25]  M. Nechaev,et al.  Solvent‐Free Buchwald–Hartwig Reaction of Aryl and Heteroaryl Halides with Secondary Amines , 2014 .

[26]  Shuainan Liu,et al.  Design, synthesis and biological evaluation of 7-nitro-1H-indole-2-carboxylic acid derivatives as allosteric inhibitors of fructose-1,6-bisphosphatase. , 2014, Bioorganic & medicinal chemistry.

[27]  I. Hardcastle,et al.  Trifluoroacetic acid in 2,2,2-trifluoroethanol facilitates S(N)Ar reactions of heterocycles with arylamines. , 2014, Chemistry.

[28]  F. Glorius,et al.  Indolsynthese durch Rhodium(III)‐katalysierte Hydrazin‐dirigierte C‐H‐Aktivierung: redoxneutral und spurlos durch N‐N‐Bindungsspaltung , 2013 .

[29]  F. Glorius,et al.  Indole synthesis by rhodium(III)-catalyzed hydrazine-directed C-H activation: redox-neutral and traceless by N-N bond cleavage. , 2013, Angewandte Chemie.

[30]  T. Cundari,et al.  Computational study of carbon–hydrogen bond deprotonation by alkali metal superbases , 2013 .

[31]  Yong Huang,et al.  General and efficient synthesis of indoles through triazene-directed C-H annulation. , 2013, Angewandte Chemie.

[32]  Jieping Zhu,et al.  Palladium-catalyzed coupling of ortho-alkynylanilines with terminal alkynes under aerobic conditions: efficient synthesis of 2,3-disubstituted 3-alkynylindoles. , 2012, Angewandte Chemie.

[33]  Duane D. Miller,et al.  Indole molecules as inhibitors of tubulin polymerization: potential new anticancer agents. , 2012, Future medicinal chemistry.

[34]  John M. Knapp,et al.  Multicomponent assembly of highly substituted indoles by dual palladium-catalyzed coupling reactions. , 2012, Angewandte Chemie.

[35]  T. Snape,et al.  2-Arylindoles: a privileged molecular scaffold with potent, broad-ranging pharmacological activity. , 2012, Current medicinal chemistry.

[36]  F. Glorius,et al.  Effiziente und vielseitige Indol‐Synthese aus Enaminen und Iminen mithilfe dehydrierender Kreuzkupplung , 2012 .

[37]  F. Glorius,et al.  Efficient and versatile synthesis of indoles from enamines and imines by cross-dehydrogenative coupling. , 2012, Angewandte Chemie.

[38]  W. Xiao,et al.  Synthesis of indoles through highly efficient cascade reactions of sulfur ylides and N-(ortho-chloromethyl)aryl amides. , 2012, Angewandte Chemie.

[39]  D. Fairlie,et al.  Catalyst-free N-arylation using unactivated fluorobenzenes. , 2012, Angewandte Chemie.

[40]  Ye Wei,et al.  Palladium-catalyzed aerobic oxidative cyclization of N-aryl imines: indole synthesis from anilines and ketones. , 2012, Journal of the American Chemical Society.

[41]  D. Dickie,et al.  Reactions of CO2 and related heteroallenes with CF3-substituted aromatic silylamines of tin , 2012 .

[42]  David R. Stuart,et al.  The Vinyl Moiety as a Handle for Regiocontrol in the Preparation of Unsymmetrical 2,3‐Aliphatic‐Substituted Indoles and Pyrroles. , 2011 .

[43]  G. Fabrizi,et al.  Update 1 of: Synthesis and functionalization of indoles through palladium-catalyzed reactions. , 2011, Chemical reviews.

[44]  David R. Stuart,et al.  The vinyl moiety as a handle for regiocontrol in the preparation of unsymmetrical 2,3-aliphatic-substituted indoles and pyrroles. , 2011, Angewandte Chemie.

[45]  H. Neumann,et al.  A general rhodium-catalyzed cyanation of aryl and alkenyl boronic acids. , 2011, Angewandte Chemie.

[46]  David R. Stuart,et al.  Rhodium(III)-catalyzed arene and alkene C-H bond functionalization leading to indoles and pyrroles. , 2010, Journal of the American Chemical Society.

[47]  Hanane Bafqiren,et al.  Water enables transimination between hindered ketimines and β-aminoalcohols and selective protection of a vicinal diamine backbone , 2010 .

[48]  G. Fabrizi,et al.  Copper-catalyzed C-C bond formation through C-H functionalization: synthesis of multisubstituted indoles from N-aryl enaminones. , 2009, Angewandte Chemie.

[49]  N. Jiao,et al.  Indoles from simple anilines and alkynes: palladium-catalyzed C-H activation using dioxygen as the oxidant. , 2009, Angewandte Chemie.

[50]  David R. Stuart,et al.  Indole synthesis via rhodium catalyzed oxidative coupling of acetanilides and internal alkynes. , 2008, Journal of the American Chemical Society.

[51]  Robert J. Phipps,et al.  Cu(II)-catalyzed direct and site-selective arylation of indoles under mild conditions. , 2008, Journal of the American Chemical Society.

[52]  Liming Zhang,et al.  Platinum-catalyzed formation of cyclic-ketone-fused indoles from N-(2-alkynylphenyl)lactams. , 2008, Angewandte Chemie.

[53]  M. Arriortua,et al.  Regiochemistry of the microwave-assisted reaction between aromatic amines and alpha-bromoketones to yield substituted 1H-indoles. , 2008, Organic & biomolecular chemistry.

[54]  R. Cherney,et al.  Mild and general methods for the palladium-catalyzed cyanation of aryl and heteroaryl chlorides. , 2007, Organic letters.

[55]  T. Kawasaki,et al.  Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. , 2005, Natural product reports.

[56]  Jeffrey T. Kuethe,et al.  Practical methodologies for the synthesis of indoles. , 2006, Chemical reviews.

[57]  R. Larock,et al.  Synthesis of Heterocycles via Palladium π-Olefin and π-Alkyne Chemistry , 2004 .

[58]  Sven Doye,et al.  Ein flexibles katalytisches Eintopfverfahren zur Synthese von Indolen , 2003 .

[59]  H. Siebeneicher,et al.  A flexible and catalytic one-pot procedure for the synthesis of indoles. , 2003, Angewandte Chemie.

[60]  M. Trincado,et al.  IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes: direct assembly of 3-iodoindole cores. , 2003, Angewandte Chemie.

[61]  P. Junk,et al.  Pyridyl donor induced 1,3-silyl migration in metal complexes of the guanidine CyHNC{N(SiMe3)Py}NCy, Py = 2-(6-MeC5H3N) , 2003 .

[62]  D. O’Shea,et al.  New organolithium addition methodology to diversely functionalized indoles. , 2003, Journal of the American Chemical Society.

[63]  R. Larock,et al.  Synthesis of 2,3-Disubstituted Indoles via Palladium-Catalyzed Annulation of Internal Alkynes , 1998 .

[64]  G. Yap,et al.  N-Substituted Guanidinate Anions as Ancillary Ligands in Organolanthanide Chemistry. Synthesis and Characterization of {CyNC[N(SiMe3)2]NCy}2SmCH(SiMe3)2 , 1998 .

[65]  J. Hartwig,et al.  Palladium-Catalyzed C−N(sp2) Bond Formation: N-Arylation of Aromatic and Unsaturated Nitrogen and the Reductive Elimination Chemistry of Palladium Azolyl and Methyleneamido Complexes , 1998 .

[66]  U. Pieper,et al.  .eta.3 and .eta.6 Bridging cations in the N,N,N',N'',N''-pentamethyldiethylenetriamine-solvated complexes of benzylpotassium and benzylrubidium: an x-ray, NMR, and MO study , 1994 .

[67]  R. Larock,et al.  Synthesis of indoles via palladium-catalyzed heteroannulation of internal alkynes , 1991 .

[68]  F. G. Bordwell,et al.  Equilibrium Acidities in Dimethyl Sulfoxide Solution , 1988 .

[69]  R. R. Fraser,et al.  Acidity measurements on pyridines in tetrahydrofuran using lithiated silylamines , 1985 .

[70]  L. Hegedus,et al.  Palladium-catalyzed reactions in the synthesis of 3- and 4-substituted indoles. Approaches to ergot alkaloids , 1984 .

[71]  M. O'donnell,et al.  A mild and efficient route to Schiff base derivatives of amino acids , 1982 .

[72]  J. Bozell,et al.  Palladium-assisted intramolecular amination of olefins. Synthesis of nitrogen heterocycles , 1978 .

[73]  L. Hegedus,et al.  Palladium assisted intramolecular amination of olefins. A new synthesis of indoles , 1976 .

[74]  P. G. Gassman,et al.  Use of halogen-sulfide complexes in the synthesis of indoles, oxindoles, and alkylated aromatic amines , 1973 .

[75]  W. Madelung Über eine neue Darstellungsweise für substituierte Indole. I , 1912 .

[76]  Arnold Reissert Einwirkung von Oxalester und Natriumäthylat auf Nitrotoluole. Synthese nitrirter Phenylbrenztraubensäuren , 1897 .

[77]  E. Fischer,et al.  Synthese von Indolderivaten , 1884 .

[78]  R. Möhlau Ueber die Einwirkung primärer aromatischer Aminbasen auf Acetophenonbromid , 1881 .