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
收藏
页码：15276 / 15280
页数：5
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