17324-04-8Relevant articles and documents
Synthesis and structural analysis of oligo(naphthalene-2,3-diyl)s
Motomura, Takahisa,Nakamura, Hideko,Suginome, Michinori,Murakami, Masahiro,Ito, Yoshihiko
, p. 142 - 146 (2005)
Oligo(naphthalene-2,3-diyl)s are synthesized by the palladium-catalyzed cross-coupling reactions of 2-naphthyl-zinc compounds with 2-bromonaphthalene derivatives. An NMR analysis together with an X-ray diffraction study supports the conjecture that the helical secondary structure is a common feature of the assemblies in which naphthalene-like aromatic units are linked together between the β-positions in series.
Synthesis of Phenacene-Helicene Hybrids by Directed Remote Metalation
Kancherla, Sindhu,J?rgensen, K?re B.
supporting information, p. 11140 - 11153 (2020/11/20)
Polycyclic aromatic hydrocarbons (PAHs) with six and seven rings were synthesized via directed metalation and cross-coupling of chrysenyl N,N-diethyl carboxamides with o-tolyl and methylnaphthalenyl derivatives. In the presence of competing ortho sites, the site selectivity in iodination of chrysenyl amides by directed ortho metalation (DoM) was influenced by the lithium base. The catalyst ligand bite angle was presumably important in the cross-coupling of sterically hindered bulky PAHs. Subsequent directed remote metalation of biaryls under standard conditions and at elevated temperatures afforded various fused six- and seven-ring PAHs, all in good yields and with fluorescent properties.
The ketene-surrogate coupling: Catalytic conversion of aryl iodides into aryl ketenes through ynol ethers
Zhang, Wenhan,Ready, Joseph M.
supporting information, p. 8980 - 8984 (2014/11/07)
tert-Butoxyacetylene is shown to undergo Sonogashira coupling with aryl iodides to yield aryl-substituted tert-butyl ynol ethers. These intermediates participate in a [1,5]-hydride shift, which results in the extrusion of isobutylene and the generation of aryl ketenes. The ketenes are trapped in situ with multiple nucleophiles or undergo electrocyclic ring closure to yield hydroxynaphthalenes and quinolines.
