Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H2O2-POCl3 system

被引：46

作者：

Bahrami, Kiumars ^{[1
,2
]}

Khodaei, Mohammad M. ^{[1
,2
]}

Abbasi, Jamshid ^{[1
]}

机构：

[1] Razi Univ, Fac Chem, Dept Organ Chem, Kermanshah 6714967346, Iran

[2] Razi Univ, NNRC, Kermanshah 6714967346, Iran

来源：

TETRAHEDRON | 2012年 / 68卷 / 25期

关键词：

NUCLEOPHILIC-SUBSTITUTION REACTIONS; EXCHANGE-RESINS; SELECTIVE OXIDATION; ARYL; ANTICANCER; CONVERSION; SULFIDES; ACID; SULFONYLBENZOTRIAZOLES; SULFOXIDES;

D O I：

10.1016/j.tet.2012.04.040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phosphorus oxychloride efficiently promoted the synthesis of sulfonamides and sulfonic esters from thiols with hydrogen peroxide in the presence of Amberlite IRA-400 (OH-). This method has been applied to a variety of substrates including nucleophilic and sterically hindered amines, and also phenols with excellent yields of sulfonamides and sulfonic esters. In most cases these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5095 / 5101

页数：7

共 80 条

[1] Ion-Exchange Resins: A Retrospective from Industrial and Engineering Chemistry Research
Alexandratos, Spiro D.
[J]. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2009, 48 (01) : 388 - 398
[2] Anderson K.K., 1979, COMPREHENSIVE ORGANI, V3
[3] CATION-EXCHANGE RESIN CATALYZED HYDROLYSIS AND DECARBOXYLATION OF ESTERS OF ACETOACETIC AND MALONIC ACIDS
ASTLE, MJ
OSCAR, JA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (06) : 1713 - &
[4] Selective oxidation of sulfides to sulfoxides and sulfones using hydrogen peroxide (H2O2) in the presence of zirconium tetrachloride
Bahrami, K
[J]. TETRAHEDRON LETTERS, 2006, 47 (12) : 2009 - 2012
[5] Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles
Bahrami, Kiumars
Khodaei, M. Mehdi
Naali, Fardin
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) : 6835 - 6837
[6] A simple and efficient one-pot synthesis of 2-substituted benzimidazoles
Bahrami, Kiumars
Khodaei, Mohammad Mehdi
Kavianinia, Iman
[J]. SYNTHESIS-STUTTGART, 2007, (04): : 547 - 550
[7] SBA-15-Pr-SO3H as nanoreactor catalyzed oxidation of sulfides into sulfoxides
Bahrami, Kiumars
Khodaei, Mohammad M.
Fattahpour, Peyman
[J]. CATALYSIS SCIENCE & TECHNOLOGY, 2011, 1 (03) : 389 - 393
[8] Trimethylsilyl Chloride Promoted Selective Desulfurization of Thiocarbonyls to Carbonyls with Hydrogen Peroxide
Bahrami, Kiumars
Khodaei, Mohammad Mehdi
Tajik, Maryam
[J]. SYNTHESIS-STUTTGART, 2010, (24): : 4282 - 4286
[9] TMSCl-promoted selective oxidation of sulfides to sulfoxides with hydrogen peroxide
Bahrami, Kiumars
Khodaei, Mohammad M.
Yousefi, Behrooz H.
Arabi, Mehdi Sheikh
[J]. TETRAHEDRON LETTERS, 2010, 51 (52) : 6939 - 6941
[10] TAPC-Promoted Oxidation of Sulfides and Deoxygenation of Sulfoxides
Bahrami, Kiumars
Khodaei, Mohammad M.
Arabi, Mehdi Sheikh
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (18) : 6208 - 6213

← 1 2 3 4 5 6 7 8 →