Cross-Coupling of Amines Via Photocatalytic Denitrogenation of In Situ Generated Diazenes
Overview
Affiliations
A method for C(sp)-C(sp) cross-coupling of amines is described. Primary amines are converted to 1,2-dialkyldiazenes by treatment with -nosylhydroxylamines in the presence of atmospheric oxygen. Denitrogenation of the diazenes with an iridium photocatalyst then forges the C-C bond. The substrate scope accommodates a broad latitude of functionality, including heteroaromatics and unprotected alcohols and acids.
Hydro- and deutero-deamination of primary amines using O-diphenylphosphinylhydroxylamine.
Ma P, Guo T, Lu H Nat Commun. 2024; 15(1):10190.
PMID: 39582045 PMC: 11586428. DOI: 10.1038/s41467-024-54599-y.
Reductive deaminative cross-coupling of alkyl bistriflimides enabled by electrocatalysis.
Tao X, Lee W, Xu Z, Shu H, Wang Q, Ni S Sci Adv. 2024; 10(47):eads5410.
PMID: 39576851 PMC: 11584002. DOI: 10.1126/sciadv.ads5410.
A Unified Synthesis of Diazenes from Primary Amines Using a SuFEx/Electrochemistry Strategy.
Doktor K, Vantourout J, Michaudel Q Org Lett. 2024; 26(36):7501-7506.
PMID: 39225700 PMC: 11406575. DOI: 10.1021/acs.orglett.4c02218.
Paul S, Brown M Angew Chem Int Ed Engl. 2024; 63(37):e202408432.
PMID: 39092618 PMC: 11733801. DOI: 10.1002/anie.202408432.
Unimolecular Fragment Coupling: A New Bond-Forming Methodology via the Deletion of Atom(s).
Shimazumi R, Tobisu M JACS Au. 2024; 4(5):1676-1695.
PMID: 38818052 PMC: 11134393. DOI: 10.1021/jacsau.3c00827.