title: Iron-catalyzed chemoselective azidation of benzylic silyl ethers.
abstract: Azidation: siloxy groups derived from secondary and tertiary benzyl alcohols can be transformed into azide groups at room temperature using TMSN(3) in the presence of an iron catalyst (TMS=trimethylsilyl). Secondary and tertiary benzylic silyl ethers can be transformed in the presence of primary silyl ethers, and other reactive functional groups, such as alkyl chlorides, α,β-unsaturated esters, and aldehydes, are stable under the reaction conditions.
authors.affiliation: Laboratory of Organic Chemistry, Gifu Pharmaceutical University, Japan. sawama@gifu-pu.ac.jp
authors.forename: Yoshinari
authors.initials: Y
authors.lastname: Sawama
authors.forename: Saori
authors.initials: S
authors.lastname: Nagata
authors.forename: Yuki
authors.initials: Y
authors.lastname: Yabe
authors.forename: Kosuke
authors.initials: K
authors.lastname: Morita
authors.forename: Yasunari
authors.initials: Y
authors.lastname: Monguchi
authors.forename: Hironao
authors.initials: H
authors.lastname: Sajiki
mesh_terms: D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers; D005290:Ferric Compounds / Q000737:chemistry*; D015394:Molecular Structure; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D001386:Azides; D001593:Benzyl Compounds; D004987:Ethers; D005290:Ferric Compounds; D014297:Trimethylsilyl Compounds