Nickel-Catalyzed Arylation, Alkenylation, and Alkynylation of Unprotected Thioglycosides at Room Temperature
Nickel-Catalyzed Arylation, Alkenylation, and Alkynylation of Unprotected Thioglycosides at Room Temperature
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DOI：
10.1002/chem.201302999
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发表时间：
2013-11-04
影响因子：
4.3
通讯作者：
Messaoudi, Samir
中科院分区：
文献类型：
--
作者：
Brachet, Etienne;Brion, Jean-Daniel;Messaoudi, Samir
无保护的巯基糖苷是ni -0催化的CS与官能化（杂）芳基、烯基和炔基卤化物成键反应的有效亲核试剂。在所有情况下，对亲电伴侣的官能团耐受性都很高，硫代糖苷的端粒选择性也很高。4-甲基-7-巯基-d -纤维素生物苷（mu - cb）的合成证明了该方法的有效性。
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).