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Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes
Author(s) -
Bucher Janina,
Wurm Thomas,
Taschinski Svenja,
Sachs Eleni,
Ascough David,
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.201600987
Subject(s) - fluorene , chemistry , isomerization , aromatization , alkyne , catalysis , medicinal chemistry , photochemistry , stereochemistry , combinatorial chemistry , organic chemistry , polymer
1,5 ‐ Diyne systems bearing one terminal and one benzyl‐ or allyl‐substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold‐catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C( sp 2 )–H bond of the offered unsaturated systems. If H atoms are present in the propargylic position, a subsequent isomerization to the aromatic system takes place leading to 9 H ‐fluorene and 11 H ‐benzo[ b ]fluorene derivatives as final products. In the case of a quaternary carbon in the propargylic position no further aromatization is observed and 10 H ‐benzo[ b ]fluorene derivatives are obtained in high yield.