NIS-Assisted Aza-Friedel-Crafts Reaction with α-Carbamoysulfides as Precursors ofN-Carbamoylimines
摘要:
AbstractA general and practical N‐iodosuccinimide (NIS)‐promoted aza‐Friedel–Crafts reaction of various aromatic nucleophiles with N‐acylimines generated in situ from α‐amidosulfides to give a rapid access to highly functionalized amines is described. The newly developed methodology is very mild, fast, efficient, and complementary.
In this paper, N-Boc and N-Cbz protected alpha-branched amines are synthesized directly from commercially available aromatic/heteroaromatic compounds, aldehydes, and tert-butyl or benzyl carbamate bearing a variety of substituents. Bismuth(III) triflate is found to be a highly effective catalyst for this one-pot, three-component coupling reaction. In addition, the use of mild reaction conditions, low catalytic loading, easy removal of the N-protective group, and one-step synthesis under open-flask are advantages of the present procedure.