Nickel-Catalyzed Arylation, Alkenylation, and Alkynylation of Unprotected Thioglycosides at Room Temperature

被引：65

作者：

Brachet, Etienne ^{[1
]}

Brion, Jean-Daniel ^{[1
]}

Alami, Mouad ^{[1
]}

Messaoudi, Samir ^{[1
]}

机构：

[1] Univ Paris Sud, CNRS, Fac Pharm, Lab Chim Therapeut,LabEx LERMIT,BioCIS UMR 8076, F-92296 Chatenay Malabry, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 45期

关键词：

alkenylation; alkynylation; arylation; nickel; thioglycosides; CROSS-COUPLING REACTIONS; C-S; ARYL IODIDES; TRANSITION-METAL; DIARYL SULFIDES; EFFICIENT; HALIDES; THIOOLIGOSACCHARIDES; SELENIDES; SYSTEM;

D O I：

10.1002/chem.201302999

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Unprotected thioglycosides were effective nucleophiles for Ni-0-catalyzed CS bond-forming reaction with functionalized (hetero)aryl, alkenyl, and alkynyl halides. The functional-group tolerance on the electrophilic partner was typically high and the anomeric selectivities of the thioglycosides were high in all cases. The efficiency of this general procedure was well-demonstrated by the synthesis of 4-methyl-7-thioumbelliferyl--D-cellobioside (MUS-CB).

引用

页码：15276 / 15280

页数：5

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