Highly Regioselective Syntheses of Substituted Triphenylenes from 1,2,4-Trisubstituted Arenes via a Co-Catalyzed Intermolecular Alkyne Cyclotrimerization
- 10 May 2013
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 78 (11) , 5744-5750
Abstract
Herein, we report the development of a new method for the syntheses of substituted triphenylenes from the corresponding 1,2,4-trisubstituted arenes, which were themselves generated in a highly regioselective manner according to an intermolecular alkyne cyclotrimerization reaction that was catalyzed by a novel Co-TMTU complex. This highly regioselective reaction for the formation of 1,2,4-trisubstituted arenes will be a valuable addition to the plethora of tools already available to synthetic chemists and encourage further mechanistic studies of this important alkyne trimerization process.Keywords
This publication has 42 references indexed in Scilit:
- Total Synthesis of Sporolide BAngewandte Chemie International Edition, 2009
- DyI2 initiated mild and highly selective silyl radical-catalyzed cyclotrimerization of terminal alkynes and polymerization of MMAChemical Communications, 2006
- The First Solvent-Free Cyclotrimerization Reaction of Arylethynes Catalyzed by Rhodium PorphyrinsInorganic Chemistry, 2003
- Mechanism for the Cyclotrimerization of Alkynes and Related Reactions Catalyzed by CpRuClJournal of the American Chemical Society, 2003
- Highly Regioselective [2 + 2 + 2] Cycloaddition of Terminal Alkynes Catalyzed by η6-Arene Complexes of Titanium Supported by Dimethylsilyl-Bridged p-tert-Butyl Calix[4]arene LigandJournal of the American Chemical Society, 2000
- Metal-catalyzed alkyne cyclotrimerizations in supercritical waterOrganometallics, 1993
- Formation, fragmentation, and isomerization of titanacycle rings supported by aryloxide ligationOrganometallics, 1990
- Cobalt-catalyzed one-step assembly of B-ring aromatic steroids from acyclic precursorsJournal of the American Chemical Society, 1986
- A new approach to the construction of biphenylenes by the cobalt-catalyzed cocyclization of o-diethynylbenzenes with alkynes. Application to an iterative approach to [3]phenylene, the first member of a novel class of benzocyclobutadienoid hydrocarbonsJournal of the American Chemical Society, 1985
- The palladium(II)-induced oligomerization of acetylenes: an organometallic detective storyAccounts of Chemical Research, 1976