62378-28-3Relevant academic research and scientific papers
Palladium-catalyzed suzuki coupling with terminal alkynes - Application to the synthesis of 2,3-disubstituted benzo[b]furans
Colobert, Francoise,Castanet, Anne-Sophie,Abillard, Olivier
, p. 3334 - 3341 (2007/10/03)
The Suzuki coupling reaction between alkynylboronic esters (generated in situ from acetylenic derivatives) and aryl bromides, pyridyl bromides or vinyl bromides is reported. 5-endo-dig-iodocyclisation of o-alkynylanisoles, generated by this palladium-catalyzed Suzuki coupling reaction, was performed with N-iodosuccinimide (NIS) in the presence of BCl3. 2-Substituted 3-iodobenzo[b]furans were synthesized and transformed into 2,3-disubstituted benzo[b]furans by Suzuki coupling reactions in high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Selective syntheses of partially etherified derivatives of tetrakis(2-hydroxyphenyl)ethene. An alternative to the calix[4]arene ligand system
Fujita, Megumi,Qi, Guizhong,Verkerk, Udo H.,Dzwiniel, Trevor L.,McDonald, Robert,Stryker, Jeffrey M.
, p. 2653 - 2656 (2007/10/03)
Stereoselective syntheses of (E)- and (Z)-1,2-bis(2′-hydroxyphenyl)- bis(2′-methoxyphenyl)ethene have been developed, the former by convergent coupling of an orthogonally protected 2,2′-benzophenone derivative and the latter by selective partial dealkylat
Competition of mechanisms in the photochemical cleavage of the C-X bond of aryl-substituted vinyl halides
Galli, Carlo,Gentili, Patrizia,Guarnieri, Alessandra,Kobayashi, Shinjiro,Rappoport, Zvi
, p. 9292 - 9299 (2007/10/03)
The photolysis of aryl halides caused homolysis of the carbon-halogen bond and formation of aryl radicals. In contrast, photolysis of vinyl halides can induce both heterolysis of the C-X bond, thereby generating vinyl cations, and homolysis, giving vinyl radicals. Examples of this competition among pathways is reported here for three vinylic precursors, namely, 1,2,2- triphenylbromoethene (1), 1-phenyl-2,2-bis(o-methoxyphenyl)-1-bromoethene (11), and β-bromostyrene (19). Incursion of the photoinduced S(RN)1 process, through the intermediacy of the vinyl radical, is verified in the presence of reducing nucleophiles, such as the enolate ions of ketones, and in part with (EtO)2PO-. Conversely, incursion of the heterolytic path, and intermediacy of the vinyl cation, occurs in the presence of weak electron-donor anions, such as NO2-, N3-, and Cl-. The vinyl cation produced from 19, which is less stable than those derived from 1 and 11, gives phenylacetylene via an E1-type elimination. An estimate is provided for the intramolecular rate of interception of the vinyl cation derived from 11 by the ortho-methoxy groups of the β-o-anisyl substituents. Finally, evidence against a photoinduced electron transfer from RO- ions to vinyl halide 1 is presented.
Photochemistry of Vinyl Halides. Formation of Benzofurans by Photolysis of β-(o-Methoxyphenyl)vinyl Bromides
Suzuki, Tatsuo,Kitamura, Tsugio,Sonoda, Taka-aki,Kobayashi, Shinjiro,Taniguchi, Hiroshi
, p. 5324 - 5328 (2007/10/02)
Photolysis of β,β-bis(o-methoxyphenyl)-substituted vinyl bromides gave benzofuran derivatives which are derived from an intramolecular nucleophilic attack of the methoxyl group on an intermediate vinyl cation.With α-aryl-substituted vinyl bromides, only o
