1093944-34-3Relevant academic research and scientific papers
Combining gold and palladium catalysis: One-pot access to pentasubstituted arenes from furan-yne and En-diyne substrates
Hashmi, A. Stephen K.,Ghanbari, Mohammad,Rudolph, Matthias,Rominger, Frank
supporting information; experimental part, p. 8113 - 8119 (2012/08/28)
A series of furan-yne systems was transformed into the corresponding tetrasubstituted annelated phenol derivatives that bear one bromo group. The two-step procedure consisted of a phenol synthesis and a subsequent electrophilic bromination with N-bromosuccinimide (NBS). The reactions can be performed in a one-pot procedure with the same precatalyst. The halogenation reaction is highly selective only in the presence of the gold catalyst. En-diyne substrates were also suitable starting materials; then the pentasubstituted aromatic core showed a completely different substitution pattern for the phenolic products. Furthermore, a one-pot protocol that consisted of a gold-catalyzed phenol synthesis, a gold-catalyzed halogenation reaction, and a palladium-catalyzed Suzuki coupling was established. The overall efficiency of this procedure was excellent and the substrate scope of the reaction was broad. Copyright
Gold catalysis: Non-spirocyclic intermediates in the conversion of furanynes by the formal insertion of an alkyne into an aryl-alkyl C-C single bond
Hashmi, A. Stephen K.,Haeffner, Tobias,Yang, Weibo,Pankajakshan, Sreekumar,Schaefer, Sascha,Schultes, Lara,Rominger, Frank,Frey, Wolfgang
, p. 10480 - 10486 (2012/11/07)
It takes al-kynes: The formation of furyl-substituted heterocycles from furanynes with donor groups on the furan-alkyne tether and mechanistic control experiments indicate the involvement of open-chained carbenium ions in the overall insertion of an alkyne into a C-C bond, rather than the usual spirocyclic intermediates (see scheme). Copyright
Gold catalysis and chiral sulfoxides: Enantioselective synthesis of dihydroisoindol-4-ols
Hashmi, A. Stephen K.,Schaefer, Sascha,Bats, Jan W.,Frey, Wolfgang,Rominger, Frank
supporting information; experimental part, p. 4891 - 4899 (2009/05/30)
Furfurals and enantomerically pure sulfinamides have been condensed to N-sulfinylimines. Addition of organolithium or -magnesium compounds to these imines allowed a 1,2-induction. After propargylation, the sulfinamides gave low conversion with gold catalysts. Oxidation to chiral sulfonamides, propargylation and gold-catalysed cycloisomerization to the phenol delivered non-racemic dihydroisoindol-4-ols in good yields. In situ NMR studies prove the intermediacy of the arene oxide even with the AuCl3 catalyst. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
