52977-22-7Relevant 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 (2014)
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.
