Transition metal-catalyzed N-arylations of amidines and guanidines.

Although several recent reviews dealt with transition metal catalyzed N-arylation of amines (all classes), to date no specific review covering the N-arylation of amidines and guanidines appeared. Amidines and guanidines are considered as fundamental entities in medicinal chemistry. The appearance of these functional groups in drugs, agrochemicals and natural products justifies a separate description of the current status of the literature on the N-arylation of the amidine and guanidine functionalities. Both acyclic and cyclic derivatives are taken into account. For cyclic amidines/guanidines only systems which possess an exocyclic nitrogen atom are considered. This critical review is largely organized by the type of amidine/guanidine and transition metal used and covers literature up to May 2011 (200 references).

[1]  M. Pannala,et al.  Catalytic amination of 5-iodouracil derivatives , 2001 .

[2]  R. Batey,et al.  Copper-catalyzed domino annulation approaches to the synthesis of benzoxazoles under microwave-accelerated and conventional thermal conditions. , 2008, The Journal of organic chemistry.

[3]  P. Bailey,et al.  The coordination chemistry of guanidines and guanidinates , 2001 .

[4]  B. Maes,et al.  On the importance of an acid additive in the synthesis of pyrido[1,2-a]benzimidazoles by direct copper-catalyzed amination. , 2011, Chemistry.

[5]  M. Mąkosza,et al.  Nucleophilic substitution of hydrogen in heterocyclic chemistry. , 2004, Chemical reviews.

[6]  S. Messaoudi,et al.  A site selective C-H arylation of free-(NH2) adenines with aryl chlorides: application to the synthesis of 6,8-disubstituted adenines. , 2009, Organic & biomolecular chemistry.

[7]  S. Buchwald,et al.  Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide. , 2010, Chemical science.

[8]  S. Buchwald,et al.  A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines , 1995 .

[9]  C. Rizzo,et al.  Site-specific synthesis and properties of oligonucleotides containing C8-deoxyguanosine adducts of the dietary mutagen IQ. , 2004, Journal of the American Chemical Society.

[10]  Wei Ma,et al.  Properties of a novel acid dye 1-amino-4-[(6-nitro-2-benzothiazolyl)amino]-9,10-anthraquinone-2-sulfonic acid with anti-UV capability , 2010 .

[11]  K. Wakabayashi,et al.  Palladium-catalyzed direct N-arylation of nucleosides, nucleotides, and oligonucleotides for efficient preparation of dG-N2 adducts with carcinogenic amino-/nitroarenes. , 2006, The Journal of organic chemistry.

[12]  B. Maes,et al.  Orthogonal and auto-tandem catalysis: synthesis of dipyrido[1,2-a:2',3'-d]imidazole and its benzo and aza analogues via inter- and intramolecular C-N bond formation. , 2006, The Journal of organic chemistry.

[13]  M. Lakshman,et al.  Pd-Xantphos-catalyzed direct arylation of nucleosides. , 2006, Organic letters.

[14]  Yuyang Jiang,et al.  Copper-catalyzed synthesis of benzimidazoles via cascade reactions of o-haloacetanilide derivatives with amidine hydrochlorides. , 2008, The Journal of organic chemistry.

[15]  Hualiang Jiang,et al.  Microwave-assisted synthesis of quinazolinone derivatives by efficient and rapid iron-catalyzed cyclization in water , 2009 .

[16]  Qiang Zhu,et al.  A direct intramolecular C-H amination reaction cocatalyzed by copper(II) and iron(III) as part of an efficient route for the synthesis of pyrido[1,2-a]benzimidazoles from N-aryl-2-aminopyridines. , 2010, Journal of the American Chemical Society.

[17]  R. Dommisse,et al.  Selective palladium-catalyzed aminations on dichloropyridines , 2001 .

[18]  Fei Wang,et al.  A protocol to 2-aminobenzimidazoles via copper-catalyzed cascade addition and cyclization of o-haloanilines and carbodiimides. , 2011, The Journal of organic chemistry.

[19]  Xiaohu Deng,et al.  Reactivity-Controlled Regioselectivity: A Regiospecific Synthesis of 1,2-Disubstituted Benzimidazoles , 2010 .

[20]  M. Huffman,et al.  Pd-catalyzed N-arylation of heteroarylamines. , 2002, Organic letters.

[21]  Shiro Kobayashi,et al.  Synthetic reaction by complex catalyst. I. copper catalyzed reaction of amine with isocyanide , 1966 .

[22]  D. Boykin,et al.  Palladium-catalyzed N-arylation of O-methylamidoximes , 2002 .

[23]  G. Noronha,et al.  The design and preliminary structure-activity relationship studies of benzotriazines as potent inhibitors of Abl and Abl-T315I enzymes. , 2007, Bioorganic & medicinal chemistry letters.

[24]  K. Robeyns,et al.  Synthesis of pyrazino[1,2-a]benzimidazol-1(2H)ones via a microwave assisted Buchwald–Hartwig type reaction , 2008 .

[25]  M. Lautens,et al.  Palladium-catalyzed domino direct arylation/N-arylation: convenient synthesis of phenanthridines. , 2009, Angewandte Chemie.

[26]  Chaomin Li,et al.  A practical strategy for the synthesis of 2-dialkylamino-4-arylamino-6-aminopyrimidines , 2009 .

[27]  C. Brain,et al.  An intramolecular palladium-catalysed aryl amination reaction to produce benzimidazoles , 2002 .

[28]  S. Buchwald,et al.  C-H functionalization/C-N bond formation: copper-catalyzed synthesis of benzimidazoles from amidines. , 2008, Angewandte Chemie.

[29]  J. Ryu,et al.  Synthesis of New N-Arylpyrimidin-2-amine Derivatives Using a Palladium Catalyst , 2008, Molecules.

[30]  W. Bao,et al.  COPPER(II) ACETATE/OXYGEN-MEDIATED NUCLEOPHILIC ADDITION AND INTRAMOLECULAR C=H ACTIVATION/C = N OR C=C BOND FORMATION: ONE-POT SYNTHESIS OF BENZIMIDAZOLES OR QUINAZOLINES , 2010 .

[31]  S. Buchwald,et al.  On the role of metal contaminants in catalyses with FeCl3. , 2009, Angewandte Chemie.

[32]  Yuyang Jiang,et al.  Highly efficient copper-catalyzed cascade synthesis of quinazoline and quinazolinone derivatives. , 2008, Chemical communications.

[33]  T. Hirano,et al.  Synthesis and properties of bis(pyrazino[2′,3′:4,5]imidazole)-fused 1,2,5,6-tetrahydro-1,4,5,8,9,10-hexaazaanthracenes: a new fluorescent nitrogen-rich heterocycle , 2010 .

[34]  J. Singer,et al.  Diamino-C,N-diarylpyridine positional isomers as inhibitors of lysophosphatidic acid acyltransferase-beta. , 2005, Bioorganic & medicinal chemistry letters.

[35]  R. Rossi,et al.  Regioselective Functionalization of the Imidazole Ring via Transition Metal-Catalyzed CN and CC Bond Forming Reactions , 2010 .

[36]  J. Galy,et al.  Reactivity of 2‐Aminothiazole and 2‐ or 6‐Aminobenzothiazole Derivatives Towards the Triphenylbismuth Diacetate/Catalytic Copper Diacetate Phenylation System , 2004 .

[37]  Fangyun Hu,et al.  Copper-catalyzed intramolecular C-N bond formation: a straightforward synthesis of benzimidazole derivatives in water. , 2011, The Journal of organic chemistry.

[38]  Davidr . Evans,et al.  Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine , 1998 .

[39]  F. Glorius,et al.  Copper-catalyzed synthesis of 2-unsubstituted, N-substituted benzimidazoles. , 2009, The Journal of organic chemistry.

[40]  G. Fukin,et al.  Lanthanide Complexes Coordinated by a Dianionic Bis(amidinate) Ligand with a Rigid Naphthalene Linker , 2010 .

[41]  C. Brain,et al.  An improved procedure for the synthesis of benzimidazoles, using palladium-catalyzed aryl-amination chemistry. , 2003, The Journal of organic chemistry.

[42]  Simon Saubern,et al.  New aryl/heteroaryl CN bond cross-coupling reactions via arylboronic acid/cupric acetate arylation , 1998 .

[43]  V. Truong,et al.  Mild and efficient ligand-free copper-catalyzed condensation for the synthesis of quinazolines , 2010 .

[44]  Kaixian Chen,et al.  Ligand-free iron/copper cocatalyzed N-arylations of aryl halides with amines under microwave irradiation , 2010 .

[45]  R. Dommisse,et al.  Study of a new rate increasing "base effect" in the palladium-catalyzed amination of aryl iodides. , 2004, The Journal of organic chemistry.

[46]  J. Meyer,et al.  Reactions of an Aluminum Amide with Aromatic Nitriles: Formation of Al−N−C Frameworks , 2010 .

[47]  S. Buchwald,et al.  Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles. , 2006, Angewandte Chemie.

[48]  P. Saha,et al.  Ligand-free copper-catalyzed synthesis of substituted benzimidazoles, 2-aminobenzimidazoles, 2-aminobenzothiazoles, and benzoxazoles. , 2009, The Journal of organic chemistry.

[49]  W. Bao,et al.  Synthesis of Benzoxazole and Benzimidazole Derivatives via Ligand‐Free Copper(I)‐Catalyzed Cross‐Coupling Reaction of o‐Halophenols or o‐Haloanilines with Carbodiimides , 2010 .

[50]  B. Maes,et al.  Synthesis of new tetracyclic azaheteroaromatic cores via auto-tandem Pd-catalyzed and one-pot Pd- and Cu-catalyzed double C-N bond formation , 2010 .

[51]  T. Punniyamurthy,et al.  Copper-mediated synthesis of substituted 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles via C-H functionalization/C-N/C-O bond formation. , 2011, The Journal of organic chemistry.

[52]  D. Bethell,et al.  Kinetic and product studies on Ullmann amination of 1-halogenoanthraquinones catalysed by copper(I) salts in acetonitrile solution , 1985 .

[53]  Jonathan P. McMullen,et al.  Palladium-catalyzed amination reactions in flow: overcoming the challenges of clogging via acoustic irradiation , 2011 .

[54]  U. Scholz,et al.  Palladium‐Catalyzed CN and CO Coupling–A Practical Guide from an Industrial Vantage Point† , 2004 .

[55]  T. Ogata,et al.  Highly reactive, general and long-lived catalysts for palladium-catalyzed amination of heteroaryl and aryl chlorides, bromides, and iodides: scope and structure-activity relationships. , 2008, Journal of the American Chemical Society.

[56]  D. Ma,et al.  Enantioselective synthesis of functionalized α-amino acids via a chiral guanidine catalyzed Michael addition reaction , 1999 .

[57]  H. Ila,et al.  Palladium-catalyzed intramolecular N-arylation of heteroarenes: a novel and efficient route to benzimidazo[1,2-a]quinolines. , 2006, The Journal of organic chemistry.

[58]  Chongzhao Ran,et al.  N6-Arylation of 2'-deoxyadenosine via copper-catalyzed direct coupling with aryl halides. , 2005, The Journal of organic chemistry.

[59]  S. Buchwald,et al.  Expedited palladium-catalyzed amination of aryl nonaflates through the use of microwave-irradiation and soluble organic amine bases. , 2006, The Journal of organic chemistry.

[60]  J. Barker,et al.  The coordination chemistry of the amidine ligand , 1994 .

[61]  Michael P. Winters,et al.  New N- and O-arylations with phenylboronic acids and cupric acetate , 1998 .

[62]  S. Buchwald,et al.  Pd-catalyzed amidation of aryl chlorides using monodentate biaryl phosphine ligands: a kinetic, computational, and synthetic investigation. , 2007, Journal of the American Chemical Society.

[63]  William L. Jorgensen,et al.  Eastern extension of azoles as non-nucleoside inhibitors of HIV-1 reverse transcriptase; cyano group alternatives. , 2010, Bioorganic & medicinal chemistry letters.

[64]  P. Proksch,et al.  Chemical and pharmacological significance of natural guanidines from marine invertebrates. , 2011, Mini reviews in medicinal chemistry.

[65]  Murray Goodman,et al.  Triurethane-Protected Guanidines and Triflyldiurethane-Protected Guanidines: New Reagents for Guanidinylation Reactions , 1998 .

[66]  Jörn Lötsch,et al.  Ziconotide for treatment of severe chronic pain , 2010, The Lancet.

[67]  Yuyang Jiang,et al.  Copper-catalyzed synthesis of primary arylamines via cascade reactions of aryl halides with amidine hydrochlorides. , 2008, The Journal of organic chemistry.

[68]  D. Nocera,et al.  Spectroscopic determination of proton position in the proton-coupled electron transfer pathways of donor-acceptor supramolecule assemblies. , 2006, Journal of the American Chemical Society.

[69]  A. Pombeiro,et al.  Additions to metal-activated organonitriles. , 2002, Chemical reviews.

[70]  J. Hartwig,et al.  Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents , 1995 .

[71]  P. Cintas,et al.  SYNTHESIS OF GLYCOAMIDINES USING A MERCURY-PROMOTED REACTION , 1995 .

[72]  R. Batey,et al.  Copper- and palladium-catalyzed intramolecular aryl guanidinylation: an efficient method for the synthesis of 2-aminobenzimidazoles. , 2003, Organic letters.

[73]  G. P. V. van Klink,et al.  The mechanism of the modified Ullmann reaction. , 2010, Dalton transactions.

[74]  H. Takayama,et al.  First total synthesis of trimeric indole alkaloid, psychotrimine. , 2008, Organic letters.

[75]  A. Vasudevan,et al.  Efficient Pd-catalyzed synthesis of 2-arylaminopyrimidines via microwave irradiation , 2006 .

[76]  I. Beletskaya,et al.  Copper in cross-coupling reactions: The post-Ullmann chemistry , 2004 .

[77]  M. Chiba,et al.  Discovery and structure-activity relationships of a novel class of quinazoline glucokinase activators. , 2009, Bioorganic & medicinal chemistry letters.

[78]  Anna Wilhelmsson,et al.  1-(3-Aryloxyaryl)benzimidazole sulfones are liver X receptor agonists. , 2010, Bioorganic & medicinal chemistry letters.

[79]  T. Ogata,et al.  Palladium-catalyzed amination of aryl and heteroaryl tosylates at room temperature. , 2008, Journal of the American Chemical Society.

[80]  C. Rizzo,et al.  Synthesis of the N2-deoxyguanosine adduct of the potent dietary mutagen IQ. , 2004, Organic letters.

[81]  J. Hiratake,et al.  β-d-Glycosylamidines: potent, selective, and easily accessible β-glycosidase inhibitors , 2001 .

[82]  Steven V Ley,et al.  A flow-based synthesis of imatinib: the API of Gleevec. , 2010, Chemical communications.

[83]  P. Hitchcock,et al.  Poly(guanidyl)silanes as a new class of chelating, N-based ligand. , 2004, Dalton transactions.

[84]  R. Sreekumar,et al.  Zeolite: An efficient catalyst for the synthesis of various heterocyclic compounds , 1997 .

[85]  A. Meijere,et al.  Synthesis of 1-Substituted Benzimidazoles from o-Bromophenyl Isocyanide and Amines† , 2009 .

[86]  H. Nagasawa,et al.  Facile synthesis of 1,2,4-triazoles via a copper-catalyzed tandem addition-oxidative cyclization. , 2009, Journal of the American Chemical Society.

[87]  M. Yamashita,et al.  Organometallic chemistry of amidate complexes. accelerating effect of bidentate ligands on the reductive elimination of N-aryl amidates from palladium(II). , 2006, Journal of the American Chemical Society.

[88]  S. Ley,et al.  Modern Synthetic Methods for Copper‐Mediated C(aryl) ? O, C(aryl) ? N, and C(aryl) ? S Bond Formation , 2003 .

[89]  A. Patruno,et al.  N-Substituted acetamidines and 2-methylimidazole derivatives as selective inhibitors of neuronal nitric oxide synthase. , 2010, Bioorganic & medicinal chemistry letters.

[90]  K. Pennypacker,et al.  Copper-catalyzed guanidinylation of aryl iodides: the formation of N,N'-disubstituted guanidines. , 2010, Organic letters.

[91]  Yuyang Jiang,et al.  A simple and efficient approach to quinazolinones under mild copper-catalyzed conditions. , 2009, Angewandte Chemie.

[92]  B. Szczepankiewicz,et al.  Synthesis of purines and other fused imidazoles from acyclic amidines and guanidines. , 2005, Organic letters.

[93]  S. Buchwald,et al.  Biaryl phosphane ligands in palladium-catalyzed amination. , 2008, Angewandte Chemie.

[94]  S. Djurić,et al.  Silicon in synthesis: stabase adducts - a new primary amine protecting group: alkylation of ethyl glycinate , 1981 .

[95]  J. Kámán,et al.  Syntheses of new quinoline‐containing heterocyclic scaffolds using inter‐ and intramolecular Pd‐catalyzed amination , 2009 .

[96]  J. Hartwig,et al.  [(CyPF-(t)Bu)PdCl2]: an air-stable, one-component, highly efficient catalyst for amination of heteroaryl and aryl halides. , 2008, Organic letters.

[97]  P. Hitchcock,et al.  Coordination of neutral, methylene bridged bis-guanidyls at palladium. , 2010, Dalton Transactions.

[98]  Zhangjie Shi,et al.  Direct imidation to construct 1H-benzo[d]imidazole through Pd(II)-catalyzed C-H activation promoted by thiourea. , 2009, Chemistry.

[99]  Yan Li,et al.  A novel and practical synthesis of substituted 2-ethoxy benzimidazole: candesartan cilexetil , 2010 .

[100]  R. Dommisse,et al.  Examination of the mechanism of the intramolecular amination of N-(3 -bromopyridin -2 -yl )azaheteroarylamines and N-(2-chloropyridin-3-yl)azaheteroarylamines : a Pd-catalyzed amination and/or a base-assisted nucleophilic aromatic substitution? , 2007 .

[101]  C. Ramana,et al.  Copper-mediated coupling of aminopurines and aminopyrimidines with arylboronic acids , 2004 .

[102]  E. Anders,et al.  Synthesis of hindered chiral guanidine bases starting from (S)-(N,N-dialkyl-aminomethyl)pyrrolidines and BrCN , 2006 .

[103]  Karunakaran A Kalesh,et al.  Rapid synthesis of Abelson tyrosine kinase inhibitors using click chemistry. , 2009, Organic & biomolecular chemistry.

[104]  J. Antilla,et al.  Ligand-free copper-catalyzed arylation of amidines. , 2011, The Journal of organic chemistry.

[105]  D. Barton,et al.  Metallic copper catalysis of N-arylation of amines by triarylbismuth diacylates , 1986 .

[106]  J. Iovanna,et al.  N-aryltriazole ribonucleosides with potent antiproliferative activity against drug-resistant pancreatic cancer. , 2010, Bioorganic & medicinal chemistry letters.

[107]  Chongzhao Ran,et al.  Regioselective arylation of 2'-deoxyribonucleosides on amido or imino sites by copper(II)-mediated direct coupling with arylboronic acids , 2006 .

[108]  R. Dommisse,et al.  Synthesis of pyrido[2′,1′:2,3]imidazo[4,5-b]quinoline and pyrido[1′,2′:1,2]imidazo[4,5-b]quinoline and their benzo and aza analogs via tandem catalysis , 2007 .

[109]  P. Hitchcock,et al.  Structural diversity in the coordination of amidines and guanidines to monovalent metal halides. , 2004, Dalton transactions.

[110]  L. Moroder,et al.  N,N'-di-tert-butoxycarbonyl-1H-benzotriazole-1-carboxamidine derivatives are highly reactive guanidinylating reagents. , 2001, Organic letters.

[111]  P. Guiry,et al.  Synthesis of Quinazolinones and Quinazolines , 2005 .

[112]  Yanguang Wang,et al.  Copper‐Catalyzed One‐Pot Synthesis of Substituted Benzimidazoles , 2010 .

[113]  Hyun Ju Lee,et al.  Highly Efficient and Reusable Copper-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles with Aryl Halides , 2009, Molecules.

[114]  Yifan Liu,et al.  A Facile Total Synthesis of Imatinib Base and Its Analogues , 2008 .

[115]  Z. Hou,et al.  Catalytic addition of amine N-H bonds to carbodiimides by half-sandwich rare-earth metal complexes: efficient synthesis of substituted guanidines through amine protonolysis of rare-earth metal guanidinates. , 2007, Chemistry.

[116]  Karunakaran A Kalesh,et al.  Small molecule probes that target Abl kinase. , 2010, Chemical communications.

[117]  So Ha Lee,et al.  Design and synthesis of new anticancer pyrimidines with multiple-kinase inhibitory effect. , 2010, Bioorganic & medicinal chemistry.

[118]  A. Zentella,et al.  Synthesis and cytotoxic activity of 2-methylimidazo[1,2-a]pyridine- and quinoline-substituted 2-aminopyrimidine derivatives. , 2010, European journal of medicinal chemistry.

[119]  B. Golding,et al.  Optimisation of the synthesis of guanidines from amines via nitroguanidines using 3,5-dimethyl-N-nitro-1H-pyrazole-1-carboxamidine , 2004 .

[120]  Matthew S. Johnson,et al.  Discovery and biological evaluation of 5-aryl-2-furfuramides, potent and selective blockers of the Nav1.8 sodium channel with efficacy in models of neuropathic and inflammatory pain. , 2008, Journal of medicinal chemistry.

[121]  R. Dommisse,et al.  The first tandem double palladium-catalyzed aminations: synthesis of dipyrido[1,2-a:3',2'-d]imidazole and its benzo- and aza-analogues. , 2004, Chemical communications.

[122]  D. Hall.  Boronic acids : preparation and applications in organic synthesis and medicine , 2005 .

[123]  Xiaohu Deng,et al.  CuI-catalyzed amination of arylhalides with guanidines or amidines: a facile synthesis of 1-H-2-substituted benzimidazoles. , 2009, The Journal of organic chemistry.

[124]  Manoel T. Rodrigues,et al.  The first bismuth(III)-catalyzed guanylation of thioureas , 2006 .

[125]  H. Ila,et al.  Efficient routes to pyrazolo[3,4-b]indoles and pyrazolo[1,5-a]benzimidazoles via palladium- and copper-catalyzed intramolecular C-C and C-N bond formation. , 2009, The Journal of organic chemistry.

[126]  S. Buchwald,et al.  A highly active catalyst for Pd-catalyzed amination reactions: cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides. , 2008, Journal of the American Chemical Society.

[127]  S. Buchwald,et al.  A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles. , 2001, Journal of the American Chemical Society.

[128]  Sukbok Chang,et al.  Rhodium(NHC)-catalyzed amination of aryl bromides. , 2010, Organic letters.

[129]  M. Taillefer,et al.  Catalytic C-C, C-N, and C-O Ullmann-type coupling reactions. , 2009, Angewandte Chemie.

[130]  Hongxia Liu,et al.  Copper‐Catalyzed Synthesis of 1,2,4‐Benzothiadiazine 1,1‐Dioxide Derivatives by Coupling of 2‐Halobenzenesulfonamides with Amidines , 2009 .

[131]  Paul J. Fagan,et al.  Using Intelligent/Random Library Screening To Design Focused Libraries for the Optimization of Homogeneous Catalysts: Ullmann Ether Formation , 2000 .

[132]  J. V. Greenhill,et al.  Amidines and guanidines in medicinal chemistry. , 1993, Progress in medicinal chemistry.

[133]  S. Buchwald,et al.  Copper-catalyzed halogen exchange in aryl halides: an aromatic Finkelstein reaction. , 2002, Journal of the American Chemical Society.

[134]  P. Saha,et al.  Cobalt-catalyzed intramolecular C-N and C-O cross-coupling reactions: synthesis of benzimidazoles and benzoxazoles. , 2010, Organic & biomolecular chemistry.

[135]  F. Glorius,et al.  A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary amides into benzoxazoles , 2004 .

[136]  J. Muzart,et al.  Copper(I)-catalyzed synthesis of substituted 2-mercapto benzimidazoles. , 2009, The Journal of organic chemistry.

[137]  J. Iovanna,et al.  Cu-mediated Selective N-arylation of Aminotriazole Acyclonucleosides , 2009 .