34756-16-6Relevant articles and documents
Halogen Bond-Catalyzed Friedel?Crafts Reactions of Furans Using a 2,2’-Bipyridine-Based Catalyst
Zhang, Huimiao,Toy, Patrick H.
supporting information, p. 215 - 221 (2020/12/01)
A halogen bond donor based on a 2,2’-bipyridine framework has been synthesized, and used to catalyze Friedel?Crafts reactions of furans. Electrophiles used successfully in these reactions included various enones, an aldehyde, and a carboxylic acid anhydride. The yields of the reactions were generally good using a moderate catalyst loading (0.025 or 0.1 equiv.) at a relatively low temperature (room temp. or 50 °C) in acetonitrile. The catalyst used was designed with a biaryl scaffold so that if it indeed proved to be an efficient halogen bond donor organocatalyst, an enantioenriched version of it could potentially serve as a stereoselective catalyst. (Figure presented.).
Photooxygenation of azidoalkyl furans: Catalyst-free triazole and new endoperoxide rearrangement
Kazancioglu, Elif Akin,Kazancioglu, Mustafa Zahrittin,Fistikci, Meryem,Secen, Hasan,Altundas, Ramazan
supporting information, p. 4790 - 4793 (2013/10/08)
Photooxygenation of azidoalkyl furans has revealed both a novel triazole formation method and a unique endoperoxide rearrangement. The key step of this method is a 3 + 2 cycloaddion of the azide to the endoperoxide intermediate. The reduction of the peroxide bond and two subsequent C-C bond cleavages provide a triazole having a newly formed carboxylic acid functionality. The reactions are clean and efficient with yields ranging from 60% to 90%.
The condensation of carbonyl compounds with electron-rich arenes: Mercury, thallium, gold or a proton?
Hashmi, A. Stephen K.,Schwarz, Lothar,Rubenbauer, Philipp,Blanco, M. Carmen
, p. 705 - 708 (2007/10/03)
Gold(III) chloride, mercury(II) perchlorate, thallium(III) perchlorate and p-toluenesulfonic acid were found to efficiently catalyze the condensation of two furans with aldehydes or acetone. The olefinic unit of α,β- unsaturated carbonyl compounds reacts faster than the carbonyl group, other olefins do not react selectively. The first (addition) step is rate-limiting, the second (substitution) step is much faster.