Premium
Palladium(II)‐Catalyzed Decarboxylative Heck Arylations of Acyclic Electron‐Rich Olefins with Internal Selectivity
Author(s) -
Fardost Ashkan,
Lindh Jonas,
Sjöberg Per J. R.,
Larhed Mats
Publication year - 2014
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.201301004
Subject(s) - chemistry , palladium , heck reaction , catalysis , selectivity , organic chemistry , combinatorial chemistry , decarboxylation , photochemistry
Despite the recent emergence of decarboxylative CC bond forming reactions, methodologies providing internally arylated electron‐rich olefins are still lacking. We herein report on palladium(II)‐catalyzed decarboxylative Heck arylations of linear electron‐rich olefins with excellent selectivity for the internal position. The method allows a variety of electron‐rich linear olefins to undergo arylation with ortho ‐functionalized aromatic carboxylic acids, including heterocycles. The reaction mechanism has been explored with ESI‐MS studies to confirm previous findings, and to reveal the formation of a highly stable palladium complex as a result of the Heck product reacting with the catalyst.