A Direct Br?nsted Acid-Catalyzed Azidation of Benzhydrols and Carbohydrates
Benzhydryl alcohols were converted into their corresponding diarylazidomethane analogues using azidotrimethylsilane (TMSN3) in the presence of a catalytic amount of a Br?nsted acid HBF4·OEt2. 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.
Regier, Jeffery,Maillet, Robert,Bolshan, Yuri
p. 2390 - 2396
(2019/04/14)
Iron-catalyzed chemoselective azidation of benzylic silyl ethers
Azidation: Siloxy groups derived from secondary and tertiary benzyl alcohols can be transformed into azide groups at room temperature using TMSN3 in the presence of an iron catalyst (see scheme; TMS=trimethylsilyl). Secondary and tertiary benzy