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On the Gold‐Catalyzed Generation of Vinyl Cations from 1,5‐Diynes
Author(s) -
Wurm Thomas,
Bucher Janina,
Duckworth Sarah B.,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2017
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.201700057
Subject(s) - alkyne , catalysis , yield (engineering) , conjugated system , aryl , chemistry , combinatorial chemistry , photochemistry , medicinal chemistry , organic chemistry , materials science , polymer , alkyl , metallurgy
Conjugated 1,5‐diynes bearing two aromatic units at the alkyne termini were converted in the presence of a gold catalyst. Under mild conditions, aryl‐substituted dibenzopentalenes were generated. Calculations predict that aurated vinyl cations are key intermediates of the reaction. A bidirectional approach provided selective access to the angular annulated product in high yield, which was explained by calculations.