Visible-Light-Promoted Synthesis of 1,6-Imino Alcohols by Metal-Free 1,2-Carboimination of Alkenes

Abstract

We report a metal-free synthesis of highly functionalized 1,6-amino alcohols through a visible-light 1,2-carboimination of alkenes and bifunctional starting materials prepared from commercially available alcohols. This protocol orchestrates the generation of up to four different types of radicals, which are efficiently recombined to yield 1,6-iminyl alcohols. The methodology demonstrated a broad functional group tolerance and was validated by the late-stage installation of the 1,6-amino alcohol motif in biomolecules and pharmaceuticals and the scale-up of the process. The versatility of the products was highlighted by their conversion into a variety of useful intermediates for target-directed synthesis.