Direct access to 2-amino-5-azidomethylfurans through palladium-catalyzed azidative cycloisomerization of homoallenyl amides. Issue 36 (22nd August 2016)

• Record Type: Journal Article
• Authors: Huang, Qianwen; Zheng, Hanliang; Liu, Shuiyou; Kong, Lichun; Luo, Fang; Zhu, Gangguo
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 36(2016)
• Page Start: 8557
• Page End: 8563
• Publication Date: 2016-08-22
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob01491g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A room temperature Pd-catalyzed azidative cycloisomerization of homoallenyl amides using TMSN3 as the azidation reagent and PhI(O2 CCF3 )2 as the oxidant is described, producing various 2-amino-5-azidomethylfurans in moderate to excellent yields. Abstract : A room temperature, efficient, and palladium-catalyzed azidative cycloisomerization of homoallenyl amides using TMSN3 as the azidation reagent and PhI(O2 CCF3 )2 as the oxidant is described, producing a variety of 2-amino-5-azidomethylfurans in moderate to excellent yields. The products can be applied to the concise synthesis of 1, 2, 3-triazoles via a Cu-catalyzed azide–alkyne cycloaddition.