35453-10-2Relevant academic research and scientific papers
Two-step, practical, and diversity-oriented synthesis of multisubstituted benzofurans from phenols through Pummerer annulation followed by cross-coupling
Murakami, Kei,Yorimitsu, Hideki,Osuka, Atsuhiro
, p. 1349 - 1366 (2015/02/19)
Practical and diversity-oriented synthesis of multisubstituted benzofurans has been accomplished from simple phenols through a Pummerer annulation/cross-coupling sequence. Operationally simple and rapid reactions of phenols with ketene dithioacetal monoxides (KDMs) with the aid of trifluoroacetic anhydride provide the corresponding 2-methylsulfanylbenzo[b]furans. The scope of the reaction encompasses phenols and KDMs having a broad range of substituents. The remaining methylsulfanyl group in the annulation products is converted to various aryl groups through cross-coupling reactions that we improved specially to this end. This two-step approach to multisubstituted benzofurans is powerful enough to synthesize highly fluorescent benzofuran derivatives as well as the naturally occurring Eupomatenoid family.
Highly chemoselective oxidation of dithioester enethiolates to sulfenates: Application to the synthesis of ketene dithioacetal S-oxides
Sandrinelli, Franck,Fontaine, Gaelle,Perrio, Stephane,Beslin, Pierre
, p. 6916 - 6919 (2007/10/03)
Enethiolates derived from dithioesters were efficiently converted into the corresponding vinyl sulfenates by oxidation with a unique N-sulfonyloxaziridine 1a derived from pinacolone. Subsequent alkylation with alkyl halides led to ketene dithioacetal S-oxides in good to excellent yields.
