Iron(II)-catalyzed intramolecular olefin aminofluorination.
An iron(II)-catalyzed diastereoselective olefin aminofluorination is reported (dr up to >20:1). This new transformation applies a functionalized hydroxylamine and Et3N·3HF as the nitrogen and fluorine source, which facilitates the efficient synthesis of β-fluoro primary amines and amino acids from allylic alcohol derivatives. Preliminary mechanistic studies reveal that an iron-nitrenoid is a possible intermediate and that its reactivity and enantioselectivity can be efficiently modulated by ligands.
Department of Chemistry, Georgia State University , 100 Piedmont Avenue SE, Atlanta, Georgia 30303, United States.
Deng-Fu
DF
Lu
Guan-Sai
GS
Liu
Cheng-Liang
CL
Zhu
Bo
B
Yuan
Hao
H
Xu
D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D054879:Halogenation; D007501:Iron / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D000588:Amines; D008024:Ligands; D007501:Iron