A Direct BrOnsted Acid-Catalyzed Azidation of Benzhydrols and Carbohydrates

被引：8

作者：

Regier, Jeffery ^{[1
]}

Maillet, Robert ^{[2
]}

Bolshan, Yuri ^{[1
]}

机构：

[1] Univ Ontario Inst Technol, Fac Sci, 2000 Simcoe St North, Oshawa, ON L1H 7K4, Canada

[2] Univ Ottawa, Fac Med, 451 Smyth Rd, Ottawa, ON K1H 8M5, Canada

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 13期

基金：

加拿大自然科学与工程研究理事会;

关键词：

Azidation; Benzhydrol; Carbohydrates; BrOnsted acid; BENZYL ALCOHOLS; AZIDES; ALLYLATION; CONVERSION; CHLORIDE;

D O I：

10.1002/ejoc.201900104

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzhydryl alcohols were converted into their corresponding diarylazidomethane analogues using azidotrimethylsilane (TMSN3) in the presence of a catalytic amount of a BrOnsted acid HBF4OEt2. The azidation reactions proceeded in high yields and demonstrated excellent functional group tolerance to electron-donating and electron-withdrawing substituents. In addition, a range of unprotected functional groups including amine, amide, aldehyde and alcohol were well-tolerated. Furthermore, this methodology was successfully applied to carbohydrates for the preparation of the corresponding azide derivatives.

引用

页码：2390 / 2396

页数：7

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