A Flexible Metal-catalyzed Synthesis of Highly Substituted Aryl Phenanthrenyl selenides
SCIE
SCOPUS
- Title
- A Flexible Metal-catalyzed Synthesis of Highly Substituted Aryl Phenanthrenyl selenides
- Authors
- Wontaeck Lim; Rhee, YH
- Date Issued
- 2013-01
- Publisher
- WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
- Abstract
- 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.
- Keywords
- Homogeneous catalysis; Gold; Aromaticity; Synthetic methods; Selenium; BIS-HOMOPROPARGYLIC ALCOHOLS; UNSYMMETRICAL DIARYL; DIORGANYL SELENIDES; EFFICIENT SYNTHESIS; CYCLOISOMERIZATION; DERIVATIVES; DISELENIDES; CLEAVAGE; BENZANNULATION; DITELLURIDES
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/15971
- DOI
- 10.1002/EJOC.201201340
- ISSN
- 1434-193X
- Article Type
- Article
- Citation
- EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2013, no. 3, page. 460 - 464, 2013-01
- Files in This Item:
- There are no files associated with this item.
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.