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Direct, Chemoselective N ‐ tert ‐Prenylation of Indoles by CH Functionalization
Author(s) -
Luzung Michael R.,
Lewis Chad A.,
Baran Phil S.
Publication year - 2009
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.200902761
Subject(s) - amination , natural product , surface modification , chemistry , olefin fiber , prenylation , combinatorial chemistry , intermolecular force , ring (chemistry) , stereochemistry , organic chemistry , molecule , catalysis , enzyme
Four steps in one: The direct prenylation of indoles at N‐1 can be achieved by CH functionalization in the presence of a Pd II source. This reaction proceeds by direct intermolecular olefin amination, tolerates a broad range of functional groups, and can be carried out on a gram scale, as demonstrated by the formal syntheses of a number of natural products and the synthesis of an antifungal natural product (see scheme).