1108697-85-3Relevant academic research and scientific papers
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
supporting information, 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- and silver-catalyzed tandem amination/ring expansion of cyclopropyl methanols with sulfonamides as an expedient route to pyrrolidines
Rao, Weidong,Chan, Philip Wai Hong
experimental part, p. 10486 - 10495 (2009/10/15)
An efficient synthetic route to pyrrolidines that relies on AuCl/ AgOTf-catalyzed tandem amination/ ring expansion of substituted cyclopropyl methanols with sulfonamides is reported herein. The reactions proceed rapidly at 100 °C with catalyst loadings as low as 2 mol % and produce the pyrrolidine products in yields of 30-95%. The method was shown to be applica ble to a broad range of cyclopropyl methanols, including unactivated ones, and sulfonamide substrates containing electron-withdrawing, electron-donating, and sterically-demanding substitu ents. The mechanism is suggested to involve activation of the alcohol substrate by the AuCl/AgOTf catalyst, followed by ionization of the starting material, which causes ring opening of the cyclopropane moiety and trapping by the sulfonamide nucleophile. The resultant aminated acyclic intermediate undergoes subsequent intramolecular hydroamination to give the pyrrolidine.
