Regioselective N1- or N2-modification of benzotriazoles with iodonium salts in the presence of copper compounds

被引：6

作者：

Davydov, Dmitry V. ^{[1
]}

Chernyshev, Vladimir V. ^{[1
]}

Rybakov, Victor B. ^{[1
]}

Oprunenko, Yurii F. ^{[1
]}

Beletskaya, Irina P. ^{[1
]}

机构：

[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

来源：

MENDELEEV COMMUNICATIONS | 2018年 / 28卷 / 03期

关键词：

CATALYZED SELECTIVE ARYLATION; CROSS-COUPLING REACTIONS; C-H ACTIVATION; N-ARYLATION; DIARYLIODONIUM SALTS; 1,7-PALLADIUM MIGRATION; REDUCTIVE CYCLIZATION; HETEROCYCLES; PALLADIUM; 2-ARYL-2H-BENZOTRIAZOLES;

D O I：

10.1016/j.mencom.2018.05.019

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Modification of benzotriazoles with iodonium salts [diphenyl- and (E)-styrylphenyliodonium tosylates] occurs at the N-1- position in the presence of K2CO3 as a base and CuI as a catalyst in CH2Cl2, whereas in the presence of stoichiometric amount of [Cu-2(TMEDA)(2)(OH)(2)]Cl-2 complex regioselective N-2-modification proceeds. Two new Cu-I complexes based on benzotriazoles were synthesized and their crystal structures were determined by X-ray powder diffraction analysis.

引用

页码：287 / 289

页数：3

共 58 条

[1] Di-μ-hydroxo-bis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)] dichloride from X-ray powder data [J].

Albov, DV ;

Davydov, DV ;

Chernyshev, VV .

ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2004, 60 :M1193-M1195

[2] Photochemical C-H Activation: Generation of Indole and Carbazole Libraries, and First Total Synthesis of Clausenawalline D [J].

Alimi, Isak ;

Remy, Richard ;

Bochet, Christian G. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (22) :3197-3210

[3] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[4]

Beletskaya IP, 1998, TETRAHEDRON LETT, V39, P5621, DOI 10.1016/S0040-4039(98)01063-6

[5] Palladium- and copper-catalyzed selective arylation of 5-aryltetrazoles by diaryliodonium salts [J].

Beletskaya, IP ;

Davydov, DV ;

Gorovoy, MS .

TETRAHEDRON LETTERS, 2002, 43 (35) :6221-6223

[6] Pd- and Cu-catalyzed selective arylation of benzotriazole [J].

Beletskaya, IP ;

Davydov, DV ;

Moreno-Mañas, M .

TETRAHEDRON LETTERS, 1998, 39 (31) :5617-5620

[7] The Complementary Competitors: Palladium and Copper in C-N Cross-Coupling Reactions [J].

Beletskaya, Irina P. ;

Cheprakov, Andrei V. .

ORGANOMETALLICS, 2012, 31 (22) :7753-7808

[8] Understanding and Exploitation of Neighboring Heteroatom Effect for the Mild N-Arylation of Heterocycles with Diaryliodonium Salts under Aqueous Conditions: A Theoretical and Experimental Mechanistic Study [J].

Bihari, Tamas ;

Babinszki, Bence ;

Gonda, Zsombor ;

Kovacs, Szabolcs ;

Novak, Zoltan ;

Stirling, Andras .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (13) :5417-5422

[9] Benzotriazole: An overview on its versatile biological behavior [J].

Briguglio, I. ;

Piras, S. ;

Corona, P. ;

Gavini, E. ;

Nieddu, M. ;

Boatto, G. ;

Carta, A. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 :612-648

[10] [3+2] Cycloadditions of Azides with Arynes via Photolysis of Phthaloyl Peroxide Derivatives [J].

Chang, Denghu ;

Zhu, Dan ;

Shi, Lei .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (11) :5928-5933

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