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A Flexible Metal‐Catalyzed Synthesis of Highly Substituted Aryl Phenanthrenyl Selenides
Author(s) -
Lim Wontaeck,
Rhee Young Ho
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201340
Subject(s) - chemistry , phenanthrenes , alkyne , catalysis , selectivity , aryl , indium , yield (engineering) , combinatorial chemistry , metal , selenium , organic chemistry , phenanthrene , alkyl , materials science , metallurgy
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)/AgSbF 6 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.