A Flexible Metal-Catalyzed Synthesis of Highly Substituted Aryl Phenanthrenyl Selenides

作者：Lim Wontaeck; Rhee Young Ho^*

来源：European Journal of Organic Chemistry, 2013, (3): 460-464.

DOI：10.1002/ejoc.201201340

• Homogeneous catalysis
• Gold
• Aromaticity
• Synthetic methods
• Selenium

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 path-ways. 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.

• 出版日期2013-1