Stannous chloride as a low toxicity and extremely cheap catalyst for regio-/site-selective acylation with unusually broad substrate scope

被引：16
作者：
Lv, Jian [1 ]
Yu, Jian-Cheng [1 ]
Feng, Guang-Jing [1 ]
Luo, Tao [1 ]
Dong, Hai [1 ,2 ]
机构：
[1] Huazhong Univ Sci & Technol, Key Lab Mat Chem Energy Convers & Storage, Minist Educ, Sch Chem & Chem Engn, Luoyu Rd 1037, Wuhan 430074, Peoples R China
[2] Huazhong Univ Sci & Technol, Hubei Key Lab Bioinorgan Chem & Mat Med, Wuhan, Peoples R China
来源：
GREEN CHEMISTRY | 2020年 / 22卷 / 20期
关键词：
ACYL GROUP MIGRATION; REGIOSELECTIVE PROTECTION; CARBOHYDRATE; DIOLS; BENZOYLATION; FUNCTIONALIZATION; SPECTROSCOPY; ACETYLATION; RECOGNITION; ALKYLATION;
D O I：
10.1039/d0gc02739a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
This work reports stannous chloride (SnCl2)-catalyzed regio-/site-selective acylation with unusually broad substrate scope. In addition to 1,2- and 1,3-diols and glycosides containingcis-vicinal diol, the substrate scope also includes glycosides withoutcis-vicinal diol. For such a substrate scope, usually, only methods using stoichiometric amounts of organotin reagents can lead to the same protection pattern with high selectivities and highly isolated yields (84-97% in most cases). Therefore, SnCl2, as a low toxicity and extremely cheap reagent, should be the best catalyst for regio-/site-selective acylation compared with any previously reported reagents.
引用
收藏
页码：6936 / 6942
页数：7
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