Efficient synthesis of racemic and chiral alkenyl sulfoxides by palladium-catalyzed Suzuki coupling

被引：5

作者：

Mancha, Gisela ^{[1
]}

Cuenca, Ana B. ^{[1
]}

Rodriguez, Nuria ^{[1
]}

Medio-Simon, Mercedes ^{[1
]}

Asensio, Gregorio ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, E-46100 Valencia, Spain

来源：

TETRAHEDRON | 2010年 / 66卷 / 34期

关键词：

Palladium; Cross-coupling; Boronic acids; Sulfoxides; Suzuki reaction; VINYL SULFOXIDES; NUCLEOPHILIC EPOXIDATION; STEREOCONTROLLED PREPARATION; STEREOCHEMICAL CONTROLLERS; ASYMMETRIC-SYNTHESIS; ARYL SULFOXIDES; CONVENIENT; YLIDES;

D O I：

10.1016/j.tet.2010.06.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkenyl sulfoxide derivatives are obtained in high yields through a palladium-catalyzed Suzuki/Miyaura cross-coupling reaction of racemic and chiral 1-halo sulfoxides with aryl and alkenyl boronic acids. Chiral substrates react with no loss of optical purity and high optical yields. The reaction takes place with different palladium catalysts, such as Pd(PPh3)(4) or Pd(OAc)(2)/DABCO. Although nitrogen ligands like DABCO lead to an active palladium catalyst, they are less effective than the phosphine ones. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6901 / 6905

页数：5

共 63 条

[1]

[Anonymous], 2008, ORGANOMETALLICS

[2] Synthesis of sulfoxides by the hydrogen peroxide induced oxidation of sulfides catalyzed by iron tetrakis(pentafluorophenyl)porphyrin: Scope and chemoselectivity [J].

Baciocchi, E ;

Gerini, MF ;

Lapi, A .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3586-3589

[3]

Botella L, 2002, ANGEW CHEM INT EDIT, V41, P179, DOI 10.1002/1521-3773(20020104)41:1<179::AID-ANIE179>3.0.CO

[4]

2-O

[5] Diastereoselective synthesis of enantiopure acyclic β,β′-disubstituted vinylsulfoxides [J].

Brebion, Franck ;

Goddard, Jean-Philippe ;

Fensterbank, Louis ;

Malacria, Max .

ORGANIC LETTERS, 2008, 10 (10) :1917-1920

[6] Efficient stereochemical controllers in biaryl Suzuki coupling reactions:: Benzylic carbinols bearing in β-position thioether, dimethylamino, or sulfoxide groups [J].

Broutin, PE ;

Colobert, F .

ORGANIC LETTERS, 2005, 7 (17) :3737-3740

[7] OPTICALLY-ACTIVE SULFOXIDES BY ENANTIOSPECIFIC REACTIONS OF BROMOVINYL ARYL SULFOXIDES WITH GRIGNARD-REAGENTS [J].

CARDELLICCHIO, C ;

FIANDANESE, V ;

NASO, F ;

SCILIMATI, A .

TETRAHEDRON LETTERS, 1992, 33 (35) :5121-5124

[8] REACTIONS OF 2-HALOVINYL ARYL SULFOXIDES WITH ORGANOMETALLIC REAGENTS [J].

CARDELLICCHIO, C ;

FIANDANESE, V ;

NASO, F .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1718-1722

[9] APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS [J].

CARRENO, MC .

CHEMICAL REVIEWS, 1995, 95 (06) :1717-1760

[10]

Carreño MC, 2000, CHEM-EUR J, V6, P906

← 1 2 3 4 5 6 7 →