title: Iron-Catalyzed Direct Diazidation for a Broad Range of Olefins.
abstract: Reported herein is a new iron-catalyzed diastereoselective olefin diazidation reaction which occurs at room temperature (1-5 mol% of catalysts and d.r. values of up to >20:1). This method tolerates a broad range of both unfunctionalized and highly functionalized olefins, including those that are incompatible with existing methods. It also provides a convenient approach to vicinal primary diamines as well as other synthetically valuable nitrogen-containing building blocks which are difficult to obtain with alternative methods. Preliminary mechanistic studies suggest that the reaction may proceed through a new mechanistic pathway in which both Lewis acid activation and iron-enabled redox-catalysis are crucial for selective azido-group transfer.
authors.affiliation: Department of Chemistry, Georgia State University, 100 Piedmont Avenue SE, Atlanta, GA 30303 (USA).
authors.forename: Yong-An
authors.initials: YA
authors.lastname: Yuan
authors.affiliation: Department of Chemistry, Georgia State University, 100 Piedmont Avenue SE, Atlanta, GA 30303 (USA).
authors.forename: Deng-Fu
authors.initials: DF
authors.lastname: Lu
authors.affiliation: Department of Chemistry, Georgia State University, 100 Piedmont Avenue SE, Atlanta, GA 30303 (USA).
authors.forename: Yun-Rong
authors.initials: YR
authors.lastname: Chen
authors.affiliation: Department of Chemistry, Georgia State University, 100 Piedmont Avenue SE, Atlanta, GA 30303 (USA). hxu@gsu.edu.
authors.forename: Hao
authors.initials: H
authors.lastname: Xu
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D007501:Iron / Q000737:chemistry*
chemical_list: D000475:Alkenes; D001386:Azides; D007501:Iron
keywords: alkenes; amination; homogeneous catalysis; iron; synthetic methods