HETEROGENEOUS AND CATALYTIC THIOCYANATION OF AROMATIC COMPOUNDS IN AQUEOUS MEDIA

被引:33
作者
Zolfigol, Mohammad Ali [1 ]
Khazaei, Ardeshir [1 ]
Mokhlesi, Mohammad [1 ]
Vahedi, Hoshang [2 ]
Sajadifar, Sami [1 ,2 ]
Pirveysian, Mahtab [1 ]
机构
[1] Bu Ali Sina Univ, Fac Chem, Hamadan, Iran
[2] Payame Noor Univ, Dept Chem, Tehran 193954697, Iran
关键词
Silica sulfuric acid; silica boron sulfonic acid; thiocyanation; water; heterogeneous; SILICA SULFURIC-ACID; CARBONYL-COMPOUNDS; SULFONIC-ACID; AMMONIUM THIOCYANATE; ARYL THIOCYANATES; REGIOSELECTIVE THIOCYANATION; ELECTROPHILIC THIOCYANATION; FUNCTIONALIZED SILICA; EFFICIENT; OXIDATION;
D O I
10.1080/10426507.2011.610846
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
This article describes a highly efficient heterogeneous catalytic thiocyanation of indoles, substituted anilines (electron rich and electron deficient) and N-substituted aromatic amines in water under mild and green conditions. The reaction of substrates with KSCN in the presence of silica sulfuric acid (SSA) and silica boron sulfonic acid (SBSA) as heterogeneous catalysts and H2O2 or UHP (urea hydrogen peroxide) as green oxidants produces aryl thiocyanates in short reaction times and high yields. Moreover, in this article, some novel aryl thiocyanates were synthesized.
引用
收藏
页码:295 / 304
页数:10
相关论文
共 41 条
[11]   Chemoselective Oxidation of Sulfides with Ammonium Nitrate and Silica Sulfuric Acid Catalyzed by KBr [J].
Ghorbani-Choghamarani, Arash ;
Zolfigol, Mohammad Ali ;
Rastegar, Toktam .
CHINESE JOURNAL OF CATALYSIS, 2009, 30 (04) :273-275
[12]   THIOCYANATION OF INDOLE - SOME REACTIONS OF 3-THIOCYANOINDOLE [J].
GRANT, MS ;
SNYDER, HR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (11) :2742-2744
[13]   ARYL SELENOCYANATES AND ARYL THIOCYANATES - REAGENTS FOR PREPARATION OF ACTIVATED ESTERS [J].
GRIECO, PA ;
YOKOYAMA, Y ;
WILLIAMS, E .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (06) :1283-1285
[14]   Covalently anchored sulfonic acid onto silica as an efficient and recoverable interphase catalyst for the synthesis of 3,4-dihydropyrimidinones/thiones [J].
Gupta, Raman ;
Paul, Satya ;
Gupta, Rajive .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 266 (1-2) :50-54
[15]   Catalytic oxidation of sulfides to sulfoxides using sodium perborate and/or sodium percarbonate and silica sulfuric acid in the presence of KBr [J].
Habibi, Davood ;
Zolfigol, Mohammad Ali ;
Safaiee, Malihe ;
Shamsian, Atefeh ;
Ghorbani-Choghamarani, Arash .
CATALYSIS COMMUNICATIONS, 2009, 10 (08) :1257-1260
[16]   A new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highly selective bromination, thiocyanation or isothiocyanation of alcohols and trimethylsilyl and tetrahydropyranyl ethers [J].
Iranpoor, Nasser ;
Firouzabadi, Habib ;
Azadi, Roya .
TETRAHEDRON LETTERS, 2006, 47 (31) :5531-5534
[17]   A new application for diethyl azodicarboxylate: efficient and regioselective thiocyanation of aromatics amines [J].
Iranpoor, Nasser ;
Firouzabadi, Habib ;
Khalili, Dariush ;
Shahin, Rezvan .
TETRAHEDRON LETTERS, 2010, 51 (27) :3508-3510
[18]   Selective oxidation of sulfides to sulfoxides using 30% hydrogen peroxide catalyzed with a recoverable silica-based tungstate interphase catalyst [J].
Karimi, B ;
Ghoreishi-Nezhad, M ;
Clark, JH .
ORGANIC LETTERS, 2005, 7 (04) :625-628
[19]   Design of a highly efficient and water-tolerant sulfonic acid nanoreactor based on tunable ordered porous silica for the von Pechmann reaction [J].
Karimi, Babak ;
Zareyee, Daryoush .
ORGANIC LETTERS, 2008, 10 (18) :3989-3992
[20]   Highly chemoselective acetalization of carbonyl compounds catalyzed by a novel recyclable ammonium triflate-functionalized silica [J].
Karimi, Babak ;
Ghoreishi-Nezhad, Maryam .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 277 (1-2) :262-265