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Palladium‐Catalyzed Alkene Carboamination Reactions of Electron‐Poor Nitrogen Nucleophiles
Author(s) -
Peterson Luke J.,
Wolfe John P.
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500334
Subject(s) - alkene , chemistry , nucleophile , aryl , catalysis , yield (engineering) , palladium , medicinal chemistry , tosyl , nitrogen , organic chemistry , alkyl , materials science , metallurgy
Modified reaction conditions that facilitate Pd‐catalyzed alkene carboamination reactions of electron‐deficient nitrogen nucleophiles are reported. Pent‐4‐enylamine derivatives bearing N ‐tosyl or N ‐trifluoroacetyl groups are coupled with aryl triflates to afford substituted pyrrolidines in good yield. These reactions proceed via a mechanism involving anti ‐aminopalladation of the alkene, which differs from previously reported analogous reactions of N ‐aryl‐ and N ‐Boc‐pentenylamines. The application of these conditions to a formal synthesis of (±)‐aphanorphine is also described.