Rhodium-/Iridium-Catalyzed Hydroamination for the Synthesis of 1,2-, 1,3-, or 1,4-Diamines.

Autor: Ho AT; Department of Chemistry, University of Texas at Austin, 100 East 24 Street, Austin, TX 78741, United States., Ensign SC; Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, United States., Vanable EP; Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, United States., Portillo D; Department of Chemistry, University of Texas at Austin, 100 East 24 Street, Austin, TX 78741, United States., Humke JN; Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, United States., Kortman GD; Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, United States., Hull KL; Department of Chemistry, University of Texas at Austin, 100 East 24 Street, Austin, TX 78741, United States.; Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, United States.
Jazyk: angličtina
Zdroj: ACS catalysis [ACS Catal] 2022 Jul 15; Vol. 12 (14), pp. 8331-8340. Date of Electronic Publication: 2022 Jun 28.
DOI: 10.1021/acscatal.2c01835
Abstrakt: An Ir-catalyzed regioselective hydroamination of allyl amines using aryl amines and catalyst-controlled regiodivergent hydroamination of allylic and homoallylic amines with aniline nucleophiles are reported. The directed hydroamination reactions afford a variety of 1,2-, 1,3-, and 1,4-diamines in good to excellent yields and high regio- and chemoselectivities. Mechanistic investigations suggests that the reactions are proceeding through an oxidative addition into the ArHN-H bond and that the observed regioselectivity is due to the selective formation of a 5- or 6-membered metalacyclic intermediate, depending on the catalyst employed.
Databáze: MEDLINE