Copper-mediated simple and efficient synthesis of tribenzohexa-dehydro[12]annulene and its derivatives

A simple and efficient synthesis of tribenzohexadehydro[12]annulene and its derivatives was carried out using coupling reaction of acetylenes with iodoarenes in the presence of catalytic amounts of CuI and PPh3, together with three equivalents of K2CO3 in DMF. This synthetic procedure was applied to...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 9; pp. 1527 - 1531
Main Authors Iyoda, M, Sirinintasak, S, Nishiyama, Y, Vorasingha, A, Sultana, F, Nakao, K, Kuwatani, Y, Matsuyama, H, Yoshida, M, Miyake, Y
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 18.06.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DEHYDROBENZOANNULENES
CARBON
CATALYZED REACTION
IODINATION
annulenes
MACROCYCLIC SYSTEMS
SHAPE-PERSISTENT
cyclizations
CONJUGATION
oligomerization
macrocycles
cross-coupling
BENZO ANNULENES
COMPLEXATION
CYCLIZATION
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Summary:A simple and efficient synthesis of tribenzohexadehydro[12]annulene and its derivatives was carried out using coupling reaction of acetylenes with iodoarenes in the presence of catalytic amounts of CuI and PPh3, together with three equivalents of K2CO3 in DMF. This synthetic procedure was applied to the synthesis of a large annulenoannulene derivative.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2004-822393