[Cu(OH)(TMEDA)]₂Cl₂-catalyzed regioselective 2-arylation of 5-substituted tetrazoles with boronic acids under mild conditions.

A mild and regioselective 2-arylation of 5-substituted tetrazoles is described. The reaction proceeds regioselectively with a variety of arylboronic acids in the presence of [Cu(OH)(TMEDA)]2Cl2 to afford 2,5-disubstituted tetrazoles. This is the first report of highly regioselective arylation of 5-alkyltetrazoles.

[1]  D. Dong,et al.  The development of copper-catalyzed aerobic oxidative coupling of H-tetrazoles with boronic acids and an insight into the reaction mechanism. , 2014, Chemistry.

[2]  K. Vávrová,et al.  Synthesis and Functionalization of 5-Substituted Tetrazoles† , 2012 .

[3]  Fu‐She Han,et al.  Efficient synthesis of 2,5-disubstituted tetrazoles via the Cu2O-catalyzed aerobic oxidative direct cross-coupling of N-H free tetrazoles with boronic acids. , 2012, Chemical communications.

[4]  Jonathan Y. Mane,et al.  Synthesis and evaluation of 1,5-diaryl-substituted tetrazoles as novel selective cyclooxygenase-2 (COX-2) inhibitors. , 2011, Bioorganic & medicinal chemistry letters.

[5]  P. Patil,et al.  Three-component strategy toward 5-membered heterocycles from isocyanide dibromides. , 2011, Organic letters.

[6]  M. Krishnaiah,et al.  A Simple, Advantageous Synthesisof 5-Substituted 1H-Tetrazoles , 2010 .

[7]  S. Chandrasekhar,et al.  Solvent free synthesis of 1,5-disubstituted tetrazoles derived from Baylis Hillman acetates as potential TNF-alpha inhibitors. , 2009, Bioorganic & medicinal chemistry letters.

[8]  Qing Lin,et al.  Synthesis and evaluation of photoreactive tetrazole amino acids. , 2009, Organic letters.

[9]  Qing Lin,et al.  Convenient synthesis of highly functionalized pyrazolines via mild, photoactivated 1,3-dipolar cycloaddition. , 2007, Organic letters.

[10]  A. Katritzky,et al.  Efficient Synthesis of 1,5-Disubstituted Tetrazoles , 2007 .

[11]  N. Cosford,et al.  3-[Substituted]-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitriles: identification of highly potent and selective metabotropic glutamate subtype 5 receptor antagonists. , 2005, Bioorganic & medicinal chemistry letters.

[12]  I. Khmelinskii,et al.  Novel efficient synthesis of 3,4-dihydro-6-substituted-3-phenylpyrimidin-2(1H)-ones , 2005 .

[13]  Tao Zhou,et al.  Hypervalent iodine in synthesis 87: The synthesis of 2,5-diaryl-2H-tetrazoles , 2004 .

[14]  D. V. Davydov,et al.  Heterocyclic Derivatives of Fullerene C60. 1. Synthesis of New Fulleropyrazolines by the 1,3-Dipolar Cycloaddition of Nitrile Imines , 2004 .

[15]  D. V. Davydov,et al.  Palladium- and copper-catalyzed selective arylation of 5-aryltetrazoles by diaryliodonium salts☆ , 2002 .

[16]  D. V. Davydov,et al.  Regioselective arylation of N-tributylstannylated 5-substituted tetrazoles by diaryliodonium salts in the presence of Cu(OAc)2 , 2002 .

[17]  K. Sharpless,et al.  A click chemistry approach to tetrazoles by Huisgen 1,3-dipolar cycloaddition: synthesis of 5-sulfonyl tetrazoles from azides and sulfonyl cyanides. , 2002, Angewandte Chemie.

[18]  J. Collman,et al.  Catalytic activities of Cu(II) complexes with nitrogen-chelating bidentate ligands in the coupling of imidazoles with arylboronic acids. , 2001, The Journal of organic chemistry.

[19]  J. Collman,et al.  The [Cu(OH).TMEDA]2Cl2-catalyzed coupling of arylboronic acids with imidazoles in water. , 2001, The Journal of organic chemistry.

[20]  J. Collman,et al.  An efficient diamine.copper complex-catalyzed coupling of arylboronic acids with imidazoles , 2000, Organic letters.

[21]  A. Fedorov,et al.  N-Phenylation of azole derivatives by triphenylbismuth derivatives/cupric acetate , 1999 .

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

[23]  G. I. Koldobskii,et al.  TETRAZOLES : XXXVI. SYNTHESIS, STRUCTURE, AND PROPERTIES OF 5-NITROTETRAZOLE , 1997 .

[24]  T. V. Artamonova,et al.  Preparation of 1,5-Disubstituted Tetrazoles Under Phase-Transfer Conditions , 1996 .

[25]  E. Thomas.  The Conversion of Secondary Amides to Tetrazoles with Trifluoromethanesulfonic Anhydride and Sodium Azide , 1993 .

[26]  C. Wentrup,et al.  INTRA-MOLECULAR CYCLIZATION OF NITRILE IMINES - SYNTHESIS OF INDAZOLES, FLUORENES, AND AZA ANALOGS , 1978 .

[27]  K. Kondo,et al.  A facile synthesis of 2,5-disubstituted tetrazoles by the reaction of phenylsulfonylhydrazones with arenediazonium salts. , 1976 .

[28]  A. Kakehi,,et al.  Synthesis of 2,5-Diaryltetrazoles from N-Phenylsulfonylbenzhydrazidoyl Chlorides and Arylhydrazines , 1976 .