Tosamides alkenes

Nitrogen nucleophiles such as amines (and in intramolecular cases, amides and tosamides) readily add to alkenes complexed to palladium(ll) and iron(ll) with reactivity and regiochemical features parallel to those observed for oxygen nucleophiles. However, these metal-assisted animation reactions are subject... 

As stated above, aliphatic amines are potent ligands for electrophilic transition metals and are efficient catalyst poisons in attempted alkene animation reactions. However, tosylation of the basic amino group greatly reduces its complexing ability, yet does not compromise its ability to nucleophilically attack complexed alkenes. Thus, a variety of alkenic tosamides efficiently cyclized under palladium(II) catalysis producing N-tosylenamines in excellent yield (equations 17 and 18).32 Again, this alkene amination proceeded through an unstable a-alkylpalladium(II) species, which could be intercepted by carbon monoxide, to result in an overall aminocarbonylation of alkenes. With ureas of 3-hydroxy-4-pentenyl-amines (Scheme 7), this palladium-catalyzed process was quite efficient but it was somewhat less so with... 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ , ]

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