Aminohydroxylation of olefins with iminopyridinium ylides by dual Ir photocatalysis and Sc(OTf)3catalysis

Article abstract of DOI:10.1016/j.tet.2016.05.045

We have developed a new strategy for catalytic aminohydroxylation of olefins with an N-protected iminopyridinium ylide as the amine source. Iminopyridinium ylides N-protected with TFAc (trifluoroacetyl), Boc (tert-butoxycarbonyl), Troc (2,2,2-trichloroethoxycarbonyl), and Alloc (allyloxycarbonyl) groups serve as N-centered radical precursors when combined with fac-[Ir(ppy)₃] photocatalysis and Sc(OTf)₃catalysis. The dual Ir photoredox/Sc(OTf)₃catalysis proves to be effective for aminohydroxylation of olefins under mild reaction conditions to provide 2-aminoalcohol derivatives bearing a primary amino group.