Ready synthesis of free N-H 2-arylindoles via the copper-catalyzed amination of 2-bromo-arylacetylenes with aqueous ammonia and sequential intramolecular cyclization.

A wide range of free N-H 2-arylindoles were synthesised via the copper(II)-catalyzed amination of 2-bromo-arylacetylenes with aqueous ammonia and sequential intramolecular cyclization. The convenience and atom economy of aqueous ammonia, and the low cost of the copper catalytic system make this protocol readily superior in practical application.

[1]  M. Nazaré,et al.  A general and mild domino approach to substituted 1-aminoindoles. , 2011, Chemical communications.

[2]  G. Fabrizi,et al.  Copper catalysis in the construction of indole and benzo[b]furan rings. , 2011, Organic & biomolecular chemistry.

[3]  J. Hartwig,et al.  Catalytic organometallic reactions of ammonia. , 2011, Angewandte Chemie.

[4]  J. Renaud,et al.  Direct amination of aryl halides with ammonia. , 2010, Chemical Society reviews.

[5]  M. Stradiotto,et al.  A P,N-ligand for palladium-catalyzed ammonia arylation: coupling of deactivated aryl chlorides, chemoselective arylations, and room temperature reactions. , 2010, Angewandte Chemie.

[6]  Di Wu,et al.  A Simple and Efficient Catalytic System for Coupling Aryl Halides with Aqueous Ammonia in Water , 2010 .

[7]  M. Nazaré,et al.  A general and mild palladium-catalyzed domino reaction for the synthesis of 2H-indazoles. , 2009, Angewandte Chemie.

[8]  J. Hartwig,et al.  Palladium-catalyzed coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates: a general method for the preparation of primary arylamines. , 2009, Journal of the American Chemical Society.

[9]  Deping Wang,et al.  An Efficient Copper-Catalyzed Amination of Aryl Halides by Aqueous Ammonia , 2009 .

[10]  K. Okuma,et al.  Palladium-free zinc-mediated hydroamination of alkynes: efficient synthesis of indoles from 2-akynylaniline derivatives , 2009 .

[11]  C. Wolf,et al.  Efficient copper-catalyzed coupling of aryl chlorides, bromides and iodides with aqueous ammonia. , 2009, Chemical communications.

[12]  K. Takimiya,et al.  One-pot synthesis of benzo[b]thiophenes and benzo[b]selenophenes from o-halo-substituted ethynylbenzenes: convenient approach to mono-, bis-, and tris-chalcogenophene-annulated benzenes. , 2009, Organic letters.

[13]  Yongwen Jiang,et al.  CuI/4-hydro-L-proline as a more effective catalytic system for coupling of aryl bromides with N-boc hydrazine and aqueous ammonia. , 2009, The Journal of organic chemistry.

[14]  L. Ackermann,et al.  Copper‐Catalyzed N‐Arylation/Hydroamin(d)ation Domino Synthesis of Indoles and its Application to the Preparation of a Chek1/KDR Kinase Inhibitor Pharmacophore , 2009 .

[15]  N. Williams,et al.  Sonogashira Cross-Coupling Reactions and Construction of the Indole Ring System Using a Robust, Silica-Supported Palladium Catalyst , 2009 .

[16]  M. Willis,et al.  Tandem copper-catalysed aryl and alkenyl amination reactions: the synthesis of N-functionalised indoles. , 2009, Organic & biomolecular chemistry.

[17]  M. Taillefer,et al.  A very simple copper-catalyzed synthesis of anilines by employing aqueous ammonia. , 2009, Angewandte Chemie.

[18]  K. Kakiuchi,et al.  One-Pot/Four-Step/Palladium-Catalyzed Synthesis of Indole Derivatives: The Combination of Heterogeneous and Homogeneous Systems , 2008 .

[19]  G. Evano,et al.  Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis. , 2008, Chemical reviews.

[20]  Sukbok Chang,et al.  Ammonium salts as an inexpensive and convenient nitrogen source in the Cu-catalyzed amination of aryl halides at room temperature. , 2008, Chemical communications.

[21]  B. Kim,et al.  Indium-HI-mediated one-pot reaction of 1-(2-arylethynyl)-2-nitroarenes to 2-arylindoles , 2008 .

[22]  T. Konakahara,et al.  InBr3-promoted divergent approach to polysubstituted indoles and quinolines from 2-ethynylanilines: switch from an intramolecular cyclization to an intermolecular dimerization by a type of terminal substituent group. , 2008, The Journal of organic chemistry.

[23]  Chang-Liang Sun,et al.  Palladium-catalyzed direct arylation of (hetero)arenes with aryl boronic acids. , 2008, Angewandte Chemie.

[24]  B. Bang-Andersen,et al.  Palladium-catalyzed aryl amination-heck cyclization cascade: a one-flask approach to 3-substituted indoles. , 2008, Angewandte Chemie.

[25]  S. Marque,et al.  Iron–Palladium Association in the Preparation of Indoles and One‐Pot Synthesis of Bis(indolyl)methanes , 2007 .

[26]  S. Buchwald,et al.  Selective palladium-catalyzed arylation of ammonia: synthesis of anilines as well as symmetrical and unsymmetrical di- and triarylamines. , 2007, Journal of the American Chemical Society.

[27]  Gang Zhao,et al.  Et2Zn-catalyzed intramolecular hydroamination of alkynyl sulfonamides and the related tandem cyclization/addition reaction. , 2007, The Journal of organic chemistry.

[28]  V. Siddaiah,et al.  A facile nuclear bromination of phenols and anilines using NBS in the presence of ammonium acetate as a catalyst , 2007 .

[29]  J. Hartwig,et al.  Palladium-catalyzed coupling of ammonia and lithium amide with aryl halides. , 2006, Journal of the American Chemical Society.

[30]  C. Senanayake,et al.  A practical mild, one-pot, regiospecific synthesis of 2,3-disubstituted indoles via consecutive Sonogashira and Cacchi reactions. , 2006, Organic letters.

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

[32]  G. Fabrizi,et al.  Synthesis and functionalization of indoles through palladium-catalyzed reactions. , 2005, Chemical reviews.

[33]  T. Konakahara,et al.  Palladium-catalyzed coupling reaction of terminal alkynes with aryl iodides in the presence of indium tribromide and its application to a one-pot synthesis of 2-phenylindole. , 2004, Organic letters.

[34]  M. Taillefer,et al.  Mild Conditions for Copper‐Catalysed N‐Arylation of Pyrazoles , 2004 .

[35]  K. Hiroya,et al.  Development of an efficient procedure for indole ring synthesis from 2-ethynylaniline derivatives catalyzed by CuII salts and its application to natural product synthesis. , 2004, The Journal of organic chemistry.

[36]  P. Knochel,et al.  Synthesis of polyfunctional indoles and related heterocycles mediated by cesium and potassium bases , 2003 .