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Au I ‐Catalyzed Tandem [3,3] Rearrangement–Intramolecular Hydroarylation: Mild and Efficient Formation of Substituted Indenes
Author(s) -
Marion Nicolas,
DíezGonzález Silvia,
de Frémont Pierre,
Noble April R.,
Nolan Steven P.
Publication year - 2006
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.200600571
Subject(s) - allene , intramolecular force , trimethylsilyl , carbene , chemistry , catalysis , tandem , transformation (genetics) , medicinal chemistry , stereochemistry , annulation , combinatorial chemistry , organic chemistry , materials science , composite material , gene , biochemistry
Dignified auration : The rearrangement of phenylpropargyl acetates to substituted indenes is catalyzed by [Au I (NHC)] complexes (see scheme, NHC=N‐heterocyclic carbene) under extremely mild reaction conditions. This chemoselective transformation involves 1,3‐migration of the acetate group and is proposed to proceed through an allene intermediate. TMS=trimethylsilyl, TBS= tert ‐butyldimethylsilyl.