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The Vinyl Moiety as a Handle for Regiocontrol in the Preparation of Unsymmetrical 2,3‐Aliphatic‐Substituted Indoles and Pyrroles
Author(s) -
Huestis Malcolm P.,
Chan Lina,
Stuart David R.,
Fagnou Keith
Publication year - 2011
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.201006381
Subject(s) - regioselectivity , moiety , pyrrole , indole test , yield (engineering) , chemistry , organic chemistry , aryl , catalysis , combinatorial chemistry , materials science , alkyl , metallurgy
Rho‐Rho‐Rho your boat : A rhodium catalyst effects the regioselective oxidative coupling of enynes with N ‐aryl ureas (X=NR 2 ) and N ‐vinylacetamides (X=C(O)Me), affording the corresponding 2‐alkenylindoles and 2‐alkenylpyrroles in good yield. Simple hydrogenation delivers the C2/C3‐aliphatic‐substituted indole or pyrrole (see scheme).