Direct Conversion of Thiols to Sulfonyl Chlorides and Sulfonamides

被引：145

作者：

Bahrami, Kiumars ^{[1
,2
]}

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

Soheilizadt, Mehdi ^{[1
]}

机构：

[1] Razi Univ, Dept Chem, Kermanshah 67149, Iran

[2] Razi Univ, NNRC, Kermanshah 67149, Iran

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 24期

关键词：

SELECTIVE OXIDATION; ALPHA-DISULFOXIDE; EFFICIENT METHOD; INTERMEDIATE; INHIBITORS; SULFOXIDES; FLUORIDES; SULFIDES; SEARCH; ESTERS;

D O I：

10.1021/jo901924m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

H2O2 in combination with SOCl2 proved to be it highly reactive reagent for the direct oxidative conversion of thiol derivatives to the corresponding sulfonyl chlorides with high purity through oxidative chlorination. Upon reaction with amines, the corresponding sulfonamides were obtained in excellent yields and in very short reaction times.

引用

收藏

页码：9287 / 9291

页数：5

相关论文

共 51 条

[1]

ANDERSON K, 1979, SULFONIC ACIDS THEIR, V3

[2] Selective oxidation of sulfides to sulfoxides and sulfones using hydrogen peroxide (H2O2) in the presence of zirconium tetrachloride [J].

Bahrami, K .

TETRAHEDRON LETTERS, 2006, 47 (12) :2009-2012

[3] Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles [J].

Bahrami, Kiumars ;

Khodaei, M. Mehdi ;

Naali, Fardin .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6835-6837

[4] A simple and efficient one-pot synthesis of 2-substituted benzimidazoles [J].

Bahrami, Kiumars ;

Khodaei, Mohammad Mehdi ;

Kavianinia, Iman .

SYNTHESIS-STUTTGART, 2007, (04) :547-550

[5] H2O2/Fe(NO3)3-Promoted Synthesis of 2-Arylbenzimidazoles and 2-Arylbenzothiazoles [J].

Bahrami, Kiumars ;

Khodaei, Mohammad Mehdi ;

Naali, Fardin .

SYNLETT, 2009, (04) :569-572

[6] Desulfurization of Thioamides into Amides with H2O2/ZrCl4 Reagent System [J].

Bahrami, Kiumars ;

Khodaei, Mohammad Mehdi ;

Tirandaz, Yeganeh .

SYNTHESIS-STUTTGART, 2009, (03) :369-371

[7]

BARBERO M, 1989, SYNTHESIS-STUTTGART, P957

[8] A new, mild preparation of sulfonyl chlorides [J].

Blotny, G .

TETRAHEDRON LETTERS, 2003, 44 (07) :1499-1501

[9] Heterocyclic pentafluorophenyl sulfonate esters as shelf stable alternatives to sulfonyl chlorides [J].

Bornholdt, Jan ;

Fjaere, Karianne Wilhemsen ;

Felding, Jakob ;

Kristensen, Jesper Langgaard .

TETRAHEDRON, 2009, 65 (45) :9280-9284

[10] Palladium-catalyzed intermolecular coupling of aryl chlorides and sulfonamides under microwave irradiation [J].

Burton, G ;

Cao, P ;

Li, G ;

Rivero, R .

ORGANIC LETTERS, 2003, 5 (23) :4373-4376

← 1 2 3 4 5 6 →