Cyclopentadiene-Phosphine/Palladium-Catalyzed Cleavage of C-N Bonds in Secondary Amines: Synthesis of Pyrrole and Indole Derivatives from Secondary Amines and Alkenyl or Aryl Dibromides

An efficient Pd-catalyzed cleavage of C(sp(3))-N bonds in secondary amines and a consequent C(sp(2))-N and C(sp(3))-N coupling process was developed. Various secondary amines could be used to react with alkenyl or aryl dibromides, affording pyrroles and indoles in high yields. Cyclopentadiene-phosphine ligands, a new type of P-olefin ligand, were found to be able to promote the efficiency of this Pd-catalyzed process remarkably. A reactive Pd complex coordinated with a cyclopentadiene-phosphine ligand was successfully isolated and structurally characterized.http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000312430700006&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=8e1609b174ce4e31116a60747a720701Chemistry, MultidisciplinarySCI(E)PubMed49ARTICLE5020230-2023313