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Synthesis of Silaphenalenes by Ruthenium‐Catalyzed Annulation between 1‐Naphthylsilanes and Internal Alkynes through CH Bond Cleavage
Author(s) -
Tokoro Yuichiro,
Sugita Kengo,
Fukuzawa Shinichi
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502746
Subject(s) - annulation , chemistry , ruthenium , alkyl , catalysis , cleavage (geology) , aryl , naphthalene , bond cleavage , silanes , medicinal chemistry , yield (engineering) , substrate (aquarium) , organic chemistry , materials science , silane , biology , fracture (geology) , metallurgy , composite material , ecology
Ruthenium‐catalyzed annulation of 1‐naphthylsilanes with internal alkynes afforded silaphenalenes through cleavage of the CH bond at the 8‐position of the naphthalene. [RuH 2 (CO){P( p ‐FC 6 H 4 ) 3 } 3 ] efficiently catalyzed the reaction. The use of 1‐naphthyldiphenylsilane as a substrate resulted in a better yield of the annulation product compared to the use of silanes with alkyl groups on the silicon atom. Internal alkynes with both aryl and alkyl groups were tolerated in this reaction.