1093944-33-2Relevant academic research and scientific papers
From Furan-Yne Systems to para -Benzoquinone Derivatives: Gold-Catalyzed Cyclization and Oxidation, and Further Reduction by Sodium Dithionate
Ahmadi, Saman,Ghanbari, Mohammad
, p. 775 - 784 (2020/10/13)
A series of furan-yne systems were transformed into the corresponding para -benzoquinone derivatives by gold(ΙΙΙ) catalyst. The two-step procedure consisted of a phenol synthesis and subsequent oxidation with iodobenzene diacetate. The reactions can be carried out in a one-pot procedure with the same precatalyst. The para -benzoquinone could simply be converted into the corresponding hydroquinones by reduction with sodium dithionate. This protocol features high efficiency, mild conditions, and wide substrate scopes.
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
, 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 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.
