Palladium-catalyzed diamination of unactivated alkenes using N-fluorobenzenesulfonimide as source of electrophilic nitrogen.
A remarkable Pd-catalyzed diamination of unactivated alkenes using N-fluorobenzenesulfonimide (NFBS) as an aminating reagent is described. The reaction occurs in an intra/intermolecular fashion, incorporating one nitrogen donor from the substrate and the other from the NFBS, thereby generating cyclic diamine derivatives in a single step. The products are differentially protected at both nitrogens, allowing for maximal synthetic flexibility. The intermediacy of the Pd(IV) species is proposed to be responsible for the unusual reactivity of NFBS.
Sibbald
Paul A
PA
Department of Chemistry, University of Washington, Box 351700, Seattle, Washington 98195-1700, USA.
Michael
Forrest E
FE
D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*; D000096926:Benzenesulfonamides
D000475:Alkenes; D000588:Amines; D009584:Nitrogen; D010165:Palladium; D013449:Sulfonamides; C523711:N-fluorobenzenesulfonimide; D000096926:Benzenesulfonamides