14174-34-6Relevant academic research and scientific papers
Pd/C as a catalyst for completely regioselective c=h functionalization of thiophenes under mild conditions
Tang, Dan-Tam D.,Collins, Karl D.,Ernst, Johannes B.,Glorius, Frank
supporting information, p. 1809 - 1813 (2014/03/21)
The completely C3-selective arylation of thiophenes and benzo[b]thiophenes was achieved by using Pd/C as a heterogeneous catalyst without ligands or additives under mild reaction conditions. The practicability of this transformation is demonstrated by notable functional group tolerance and the insensitivity of the reaction to H2O and air. This method is also applicable to nitrogen- and oxygen-containing heterocycles, yielding the corresponding C2-arylated products. Three-phase tests along with Hg-poisoning and hot-filtration tests suggest that the catalytically active species is heterogeneous in nature. I+ can do better! Pd/C can be used without ligands or additives to catalyze the completely C3-selective arylation of diversely substituted thiophenes and benzo[b]thiophenes under mild reaction conditions. The physical nature of the catalytic species was investigated and the mechanism was studied. Relative rate data generated in a "robustness screen" were used to design a complex substrate that undergoes highly chemoselective sequential functionalization. Copyright
Pd-catalyzed β-selective direct C-H bond arylation of thiophenes with aryltrimethylsilanes
Funaki, Kenji,Sato, Tetsuo,Oi, Shuichi
supporting information, p. 6186 - 6189 (2013/02/23)
Direct arylation of thiophenes and benzothiophenes with aryltrimethylsilanes was effectively catalyzed by PdCl2(MeCN) 2 in the presence of CuCl2 as an oxidant. The reaction preferentially occurred at the β-position of both
PREPARATION OF 1-PHENYLTHIO-1,3-DIENES BY REACTION OF 2,5-DIHYDROTHIOPHENES WITH BENZYNE THROUGH FRAGMENTATION OF SULFONIUM YLIDE INTERMEDIATES
Nakayama, Juzo,Kumano, Yuichi,Hoshino, Masamatsu
, p. 847 - 850 (2007/10/02)
The reaction of a series of 2,5-dihydrothiophenes with benzyne, generated from 2-carboxybenzenediazonium chloride, affords 1-phenylthio-1,3-dienes in good yields through the fragmentation of sulfonium ylide intermediates.
GENERAL SYNTHESIS OF 2,5-DIHYDROTHIOPHENES (3-THIOLENES) FROM DIKETO SULFIDES
Nakayama, Juzo,Machida, Haruki,Hoshino, Masamatsu
, p. 1981 - 1982 (2007/10/02)
The intramolecular reductive coupling reaction of easily accesible diketo sulfides by a low-valent titanium reagent (prepared from titanium(IV) chloride and zinc powder) provides an efficient general synthesis of 2,5-dihydrothiophenes.
GENERAL SYNTHESIS OF POLYSUBSTITUTED THIOPHENES FROM DIKETO SULFIDES
Nakayama, Juzo,Machida, Haruki,Saito, Ryuji,Hoshino, Masamatsu
, p. 1983 - 1984 (2007/10/02)
Treatment of diketo sulfides with a low-valent titanium reagent at 0 deg C (in two cases at room temperature) affords 3,4-dihydroxythiolanes in good yields.The acid-catalyzed (p-toluenesulfonic acid) dehydration of the latter compounds leads to the corres
Some photochemical rearrangements of vinylcyclopentadienes. Mechanistic and exploratory organic photochemistry
Zimmerman, Howard E.,Ramsden, William D.
, p. 2592 - 2611 (2007/10/02)
The photochemistry of 2,3-diphenyl-1,4,5-trimethyl-5-vinylcyclopentadiene and 1,2-diphenyl-3,4,5-trimethyl-5-vinylcyclopentadiene was studied.The triplet of the 2,3-diphenyl isomer was found to undergo a 1,5-vinyl migration; in contrast, the 1,2-diphenyl
