Ligand effects in the synthesis of N-heterocycles by intramolecular Heck reactions.
Chemo- and regioselectivity of intramolecular Heck reactions are dependent on the type of ligand employed. Six- to eight-membered benzolactams are produced in good yields using PPh3 as ligand. In contrast, a biaryl coupling occurred preferentially under ligandless conditions to form a dihydrophenanthridine product. Conformations of the seven- and eight-membered benzolactams in the solid state were examined by X-ray crystallography.
Cropper
Emma L
EL
Department of Chemistry, Imperial College London, Exhibition Road, South Kensington SW7 2AZ, United Kingdom.
White
Andrew J P
AJ
Ford
Agnes
A
Hii
King Kuok Mimi
KK
D001555:Benzene Derivatives / Q000138:chemical synthesis; D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis; D008024:Ligands; D008968:Molecular Conformation; D009584:Nitrogen
D001555:Benzene Derivatives; D006571:Heterocyclic Compounds; D007769:Lactams; D008024:Ligands; D009584:Nitrogen