Practical olefin hydroamination with nitroarenes

The synthesis and functionalization of amines are fundamentally important in a vast range of chemical contexts. We present an amine synthesis that repurposes two simple feedstock building blocks: olefins and nitro(hetero)arenes. Using readily available reactants in an operationally simple procedure, the protocol smoothly yields secondary amines in a formal olefin hydroamination. Because of the presumed radical nature of the process, hindered amines can easily be accessed in a highly chemoselective transformation. A screen of more than 100 substrate combinations showcases tolerance of numerous unprotected functional groups such as alcohols, amines, and even boronic acids. This process is orthogonal to other…

• NS
  National Science Foundation
• BS
  Bristol-Myers Squibb
• CS
  China Scholarship Council
• P
  Pharmaron
• SI
  Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
• NI
  National Institute of General Medical Sciences

  Award: GM-097444