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Four Iodine‐Mediated Electrophilic Cyclizations of Rigid Parallel Triple Bonds Mapped from 1,8‐Dialkynylnaphthalenes
Author(s) -
Chen Xiaopeng,
Lu Ping,
Wang Yanguang
Publication year - 2011
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.201100858
Subject(s) - fluoranthene , electrophile , acenaphthylene , chemistry , dichloromethane , regioselectivity , pyridine , perylene , medicinal chemistry , photochemistry , iodine , coronene , aromatization , pyrene , organic chemistry , molecule , anthracene , solvent , catalysis
Four different types of fused arenes, including fluoranthene, indeno[2,1‐ a ]phenalene, (8 H )cyclopenta[ a ]acenaphthylene, and pyridine[ a ]acenaphthylene, were efficiently constructed through iodine‐mediated electrophilic cyclizations of 1,8‐dialkynyl naphthalenes in a single step. Theoretical calculations supported our hypothesis that these reactions had high regioselectivity. Oxidative coupling of the fluoranthene skeleton, followed by aromatization, effectively synthesized perylene derivative 14 , which emitted light at 597 nm in dichloromethane with an emission efficiency of 0.81 referred to 5,6,11,12‐tetraphenylnaphthacene as a standard.
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