A mechanistic alternative for the intramolecular hydroboration of homoallylic amine and phosphine borane complexes.
Intramolecular hydroboration is demonstrated starting from homoallylic amine boranes upon activation by iodine. The process involves a B-iodoborane complex as the intermediate and may occur via internal displacement of iodide by the alkene to generate a cationic borane-alkene pi-complex on the way to hydroboration products. The reaction can be carried out using a catalytic amount of iodine.
Scheideman
Matthew
M
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109, USA.
Shapland
Peter
P
Vedejs
Edwin
E
D000498:Allyl Compounds / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001880:Boranes / Q000138:chemical synthesis*; D010720:Phosphines / Q000737:chemistry*
D000498:Allyl Compounds; D000588:Amines; D001880:Boranes; D010720:Phosphines; C044646:phosphine