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On the Gold‐Catalyzed Generation of Phenyl Cations from 1,5‐Diynes
Author(s) -
Wurm Thomas,
Bucher Janina,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2017
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.201700231
Subject(s) - chemistry , alkyne , catalysis , enediyne , benzene , medicinal chemistry , stereochemistry , photochemistry , combinatorial chemistry , organic chemistry
Abstract cis ‐Enediyne systems bearing two non‐terminal alkyne functionalities were transformed in the presence of a gold catalyst. A selective 6‐ endo ‐ dig ‐cyclization generates mono‐aurated phenyl cation intermediates, high energy species that are able to activate even primary sp 3 ‐C–H‐bonds. Via insertion into intramolecularly offered, unactivated C–H‐bonds, penta‐substituted benzene derivatives are obtained as final products. In most cases selective insertions into the γ‐ sp 3 ‐C—H bonds of the offered tethers were observed.