1449574-38-2Relevant academic research and scientific papers
A flexible metal-catalyzed synthesis of highly substituted aryl phenanthrenyl selenides
Lim, Wontaeck,Rhee, Young Ho
supporting information, p. 460 - 464 (2013/02/25)
An efficient method for the preparation of diaryl selenides, which are important in biology and materials science, is described. Specifically, the development of highly substituted phenanthrenyl phenyl selenides 4 and 6 by metal-catalyzed cyclization of o-phenylarylalkynes species 1 was successfully performed. The selectivity for 9- and 10-selenyl phenanthrenes was perfectly controlled by indium(III) and gold(I) catalysts, and the reactions proceed through different pathways. For the In(OTf)3 catalyst system, 6-endo cyclization of alkyne 3 gives product 4 in which the selenium group is retained. In contrast, for the AuCl(IPr)/AgSbF6 catalyst system, transformation of metal-alkyne complex 2 into vinylidene-gold intermediate 5 gives product 6 in which the selenium group is migrated. Various substrates, even electronically poor substrates, can be converted into phenanthrenes with high selectivity in high yield under very mild conditions. Highly substituted 9- and 10-selenylphenanthrenes are easily prepared from the corresponding selenium-containing (o-phenylaryl)alkynes. The selectivity is perfectly controlled by indium(III) and gold(I) catalysts. Various substrates can be converted into phenanthrene derivatives with high selectivity and in good yield under very mild conditions. Copyright
