A New Dioxazolone for the Synthesis of 1,2‐Aminoalcohols via Iridium(III)‐Catalyzed C(sp³)−H Amidation

Abstract

Vicinal aminoalcohols are widespread structural motifs in bioactive molecules.W er eport the development of anew dioxazolone reagent containing ap-nitrophenyldifluoromethyl group,which1.displays agood safety profile;2.shows ar emarkably high reactivity in the oxime-directed iridium-(III)-catalyzed amidation of unactivated C(sp 3 ) À Hb onds;3 . leads to amide products whichc an be hydrolyzed under mild conditions.T he amidation reaction is mild, general and compatible with both primary CÀHb onds of tertiary and secondary alcohols,aswell as secondary CÀHbonds of cyclic secondary alcohols.T his method provides an easy access to free 1,2-aminoalcohols after efficient and mild cleavage of the oxime directing group and activated amide.

Nickel‐Catalyzed Site‐Selective Intermolecular C(sp3)−H Amidation

“…[4] A series of recent disclosures, however, have shown the potential of Ir-, [5] Ru- [6] or Rh-nitrenoids [7] to enable C(sp 3 )À H amination events via one-electron manifolds (Scheme 1, top), [8] thus offering a complementary approach to two-electron pathways [9] requiring strong oxidants and/or harsh conditions. [10] Unfortunately, these processes rely on functionalization at activated benzylic/allylic C(sp 3 )À H bonds, , [5c, 6c, 11] sterically-encumbered sites, , [7a, 12] noble metals or directing groups, [13] thus reinforcing the notion that the design of a new catalytic intermolecular C(sp 3 )À H amidation would be a particularly rewarding scenario in both academic and industrial endeavors.…”

Divergent Synthesis, Antiproliferative and Antimicrobial Studies of 1,3‐Aminoalcohol and 3‐Amino‐1,2‐Diol Based Diaminopyrimidines

“…In recent decades, considerable attention has been paid to 1,2‐aminoalcohols, [1–5] 1,3‐aminoalcohols, [6–8] and 3‐amino‐1,2‐diols, [9–14] with the latter combining the chemical properties of 1,2‐ and 1,3‐aminoalcohols. These compounds play a crucial role in numerous branches of human life sciences.…”