- Carbon networks based on dehydrobenzoannulenes. 3. Synthesis of graphyne substructures
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(equation presented) This Letter describes the synthesis of the first macrobicyclic subunits of the hypothetical all-carbon network graphyne. Key to synthetic success is an intramolecular Sonogashira cross-coupling sequence.
- Kehoe, Joshua M.,Kiley, James H.,English, Jamieson J.,Johnson, Charles A.,Petersen, Ryan C.,Haley, Michael M.
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- One-pot homo- and cross-coupling of diazanaphthalenes via C-H substitution: Synthesis of Bis- and Tris-diazanaphthalenes
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The transition metal-free coupling reactions of unactivated diazanaphthalenes were studied using only lithium tetramethylpiperidine (LiTMP) reagent. Symmetrical and nonsymmetrical bis-diazanaphthalenes were synthesized in moderate to high yield by homo- and cross-coupling of related monomers. In addition, the single-step synthesis of diquinoxalino [2,3-a: 2', 3'c] phenazine and 2,2': 3', 2″ - terquinoxaline using the appropriate equivalent amount of LiTMP was performed. The products were characterized by means of NMR spectroscopy and HRMS spectrometry.
- Ucar, Sefa,Dastan, Arif
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supporting information
p. 4013 - 4022
(2020/09/21)
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- Efficient synthesis of a complete donor/acceptor bis(aryl)diyne family
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A facile route to a family of bis(aryl)diynes containing both an electron donating pyridine ring and an electron accepting iodobenzene has been developed. The convergent synthesis involves the coupling of 2-, 3-, or 4-bromopyridine with TMS-acetylene, followed by deprotection to form the first half of the molecule. Similarly, 2-, 3-, or 4-iodoaniline was coupled to TMS-acetylene after protection of the amine group as a diethyltriazine. After conversion of the triazine to an iodine, deprotection of the acetylene and formation of the corresponding bromophenyl-acetylene, the two halves of the molecule were coupled under Cadiot-Chodkiewicz conditions. Nine new compounds were prepared, each of which was found to thermally polymerize from the melt. None of the compounds underwent photochemical polymerization in the solid-state.
- Holmes, Brian T.,Pennington, William T.,Hanks, Timothy W.
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p. 2447 - 2461
(2007/10/03)
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- It takes alkynes to make a world - New methods for dehydrobenzoannulene synthesis
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Recent advances in the assembly of dehydrobenzoannulenes (DBAs) are the subject of this account. Using in situ generated acetylenic intermediates, novel α,ω-polyynes can be easily constructed using Pd-catalyzed alkynylation methodology. Subsequent cyclization via intra- and intermolecular Cu-mediated reactions can provide a wide variety of DBAs, including heretofore inaccessible topologies, systems with an unprecedented number of acetylenic linkages, structures with derivatized aromatic rings, and unusual organometallic species.
- Haley, Michael M.
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p. 557 - 565
(2007/10/03)
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