Diarylamine Synthesis Via Desulfinylative Smiles Rearrangement
Overview
Chemistry
Affiliations
Diarylamines are obtained directly from sulfinamides through a novel rearrangement sequence. The transformation is transition metal-free and proceeds under mild conditions, providing facile access to highly sterically hindered diarylamines that are otherwise inaccessible by traditional SAr chemistry. The reaction highlights the distinct reactivity of the sulfinamide group in Smiles rearrangements versus that of the more common sulfonamides.
Synthesis of Diarylamines via Nitrosonium-Initiated C-N Bond Formation.
Chen P, Hsu S, Chen C, Fu J, Hou D J Org Chem. 2024; 89(14):10316-10326.
PMID: 38950197 PMC: 11267615. DOI: 10.1021/acs.joc.4c01220.
Synthesis of Functionalized Pyrrolidinone Scaffolds via Smiles-Truce Cascade.
Sephton T, Large J, Butterworth S, Greaney M Org Lett. 2023; 25(36):6736-6740.
PMID: 37668613 PMC: 10510726. DOI: 10.1021/acs.orglett.3c02559.
An NHC-Catalyzed Desulfonylative Smiles Rearrangement of Pyrrole and Indole Carboxaldehydes.
Swaby C, Taylor A, Greaney M J Org Chem. 2023; 88(17):12821-12825.
PMID: 37589318 PMC: 10476196. DOI: 10.1021/acs.joc.3c01089.
Sirakanyan S, Spinelli D, Geronikaki A, Zuppiroli L, Zuppiroli R, Kartsev V Int J Mol Sci. 2022; 23(11).
PMID: 35682584 PMC: 9179986. DOI: 10.3390/ijms23115904.