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Palladium‐Catalyzed Intermolecular Alkenylation of Indoles by Solvent‐Controlled Regioselective CH Functionalization
Author(s) -
Grimster Neil P.,
Gauntlett Carolyn,
Godfrey Christopher R. A.,
Gaunt Matthew J.
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200500468
Subject(s) - regioselectivity , intermolecular force , surface modification , palladium , catalysis , derivatization , chemistry , solvent , acetic acid , combinatorial chemistry , organic chemistry , molecule , high performance liquid chromatography
Either the C2‐ or the C3‐substituted product can be obtained with the same palladium( II ) catalyst in an oxidative intermolecular alkenylation of indoles. A variety of conditions can be used for derivatization at the 3‐position; however, the presence of acetic acid is required for the C2‐selective process (see scheme). Further elaboration of the products by a similar CH functionalization process leads to the bisalkenylated indoles selectively.