Premium
Synthesis of Single and Double Dibenzohelicenes by Rhodium‐Catalyzed Intramolecular [2+2+2] and [2+1+2+1] Cycloaddition
Author(s) -
Yamano Ryota,
Shibata Yu,
Tanaka Ken
Publication year - 2018
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.201706008
Subject(s) - helicene , cycloaddition , intramolecular force , chemistry , rhodium , enantioselective synthesis , quantum yield , yield (engineering) , catalysis , ligand (biochemistry) , fluorescence , binap , stereochemistry , medicinal chemistry , photochemistry , organic chemistry , materials science , molecule , receptor , biochemistry , physics , quantum mechanics , metallurgy
Dibenzo[7]helicenes were synthesized with up to 99 % ee by rhodium(I)/binap‐catalyzed enantioselective intramolecular [2+2+2] cycloaddition of 2‐phenylnaphthalene‐linked triynes. Additionally, [2+1+2+1] cycloaddition products, that is, twisted anthracenes, were also synthesized by using difluorphos as ligand. Although these compounds are not configurationally stable at elevated temperature, their Scholl reactions afforded configurationally stable double dibenzo[6]helicenes. The thus‐obtained dibenzo[7]helicene exhibited good circularly polarized luminescence property and the double dibenzo[6]helicene showed high fluorescence quantum yield.