Hydrogen-bond activation enables aziridination of unactivated olefins with simple iminoiodinanes

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2305 - 2312

Published: Sept. 11, 2024

Iminoiodinanes comprise a class of hypervalent iodine reagents that is often encountered in nitrogen-group transfer (NGT) catalysis. In general, transition metal catalysts are required to effect efficient NGT unactivated olefins because iminoiodinanes insufficiently electrophilic engage direct aziridination chemistry. Here, we demonstrate 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) activates N -arylsulfonamide-derived for the metal-free olefins. 1 H NMR and cyclic voltammetry (CV) studies indicate hydrogen-bonding between HFIP iminoiodinane generates an oxidant capable Stereochemical scrambling during 1,2-disubstituted observed interpreted as evidence proceeds via carbocation intermediate subsequently cyclizes. These results simple method activating reagents, provide analysis extent activation achieved by H-bonding, potential chemical non-innocence fluorinated alcohol solvents

Language: Английский

Hydroxylamine‐O‐Sulfonic Acid (HOSA): A Recent Synthetic Overview

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(35)

Published: Sept. 12, 2024

Abstract Hydroxylamine‐ O‐ sulfonic acid has been used as a versatile nitrogen source in synthetic organic chemistry. It dual function and utilized both nucleophile an electrophile during different transformations. This reagent is stable easy to handle aqueous solvents. can be with functional groups under mild reaction conditions, making its widely applicable for constructing complex molecules. various applications such agrochemicals, pharmaceuticals, polymer industries the formation of S−N, C−N, O−N, N−N bonds, well efficient cyclization reactions metal‐free conditions excellent stereo– regioselectivity. The present review provides brief overview all advancements made past two decades using hydroxylamine‐ source.

Language: Английский