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

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