89209-02-9Relevant academic research and scientific papers
Biomimetic carbene cascades enabled imine derivative migration from carbene -bearing thiocarbamates
Li, Xue,Chen, Haohua,Xuan, Qingqing,Mai, Shaoyu,Lan, Yu,Song, Qiuling
supporting information, p. 3518 - 3523 (2021/05/29)
Inspired by the body circulation of Omeprazole (irreversible proton pump inhibitor), we disclose the carbene-triggered cascades for the synthesis of 2-aminobenzofuran derivatives from N-sulfonyl-1,2,3-triazoles or benzothioazole-bearing thiocarbamates, which represents an unprecedented imine derivative migration process. Furthermore, the desulfurizing reagent-free Barton-Kellogg-type reactions starting from N-sulfonyl-1,2,3-triazoles have also been achieved for the first time, and elemental sulfur is confirmed as a byproduct during this transformation. Both experimental data and DFT calculations further thoroughly explained the unique reactivity.
O -aryloxide-N-heterocyclic carbenes: Efficient synthesis of the proligands and their p -cymene ruthenium complexes
Yang, Dandan,Tang, Yungang,Song, Haibin,Wang, Baiquan
, p. 2012 - 2017 (2015/06/08)
An efficient method to synthesize o-hydroxyaryl-substituted imidazoles (2-OH-3-R-5-tBuC6H2)(C3H3N2) [R = tBu (1a), H (1b)] was developed through copper-catalyzed C-N bond formation. Treatment of 1a or 1b with a halohydrocarbon in refluxing toluene afforded a series of o-hydroxyaryl imidazolinium proligands 2a-h in high yields. Reactions of proligands 2a-h with Ag2O and [(p-cymene)RuCl2]2 gave the corresponding o-aryloxide-N-heterocyclic carbene ligated p-cymene ruthenium complexes 3a-h. All the imidazolium salts and ruthenium complexes were fully characterized by 1H and 13C NMR spectra, elemental analysis, and high-resolution mass spectrometry. Without the cocatalyst or irradiation, these complexes can efficiently catalyze norbornene ring-opening metathesis polymerization. Notably, the structures of the catalysts were found to have significant effects on the catalytic activity and the properties of obtained polymers.
Mild and efficient oxy-iodination of alkynes and phenols with potassium iodide and tert-butyl hydroperoxide
Rajender Reddy,Venkateshwar,Uma Maheswari,Santhosh Kumar
supporting information; experimental part, p. 2170 - 2173 (2010/06/14)
An efficient synthesis of 1-iodoalkynes and iodophenols was easily achieved by employing simple KI and TBHP. The reaction does not involve the use of a metal and base combination. A variety of substituted alkynes and phenols were prepared with good to excellent yield.
Steric buttressing in the Pauson-Khand reactions of aryl enynes
Madu, Christian E.,Seshadri, Hemalatha,Lovely, Carl J.
, p. 5019 - 5029 (2008/02/01)
A variety of aryl enynes have been constructed from o-iodophenol derivatives containing ortho-tert-butyl groups via O-alkylation and a Sonogashira cross-coupling reaction. These substrates undergo efficient thermal and oxidative intramolecular Pauson-Khand reactions leading to the formation of sterically congested cyclopentenones, as well as the formation of medium-sized rings, although in the latter case with unusual regioselectivity. Incorporation of a TMS moiety on the alkyne group in a higher homolog led to cyclization via the normal mode, albeit in relatively low yield.
Design, synthesis, and structure - Activity relationship studies of novel 6,7-locked-[7-(2-alkoxy-3,5-dialkylbenzene)-3-methylocta]-2,4,6-trienoic acids
Michellys, Pierre-Yves,Ardecky, Robert J.,Chen, Jyun-Hung,D'Arrigo, Jennifer,Grese, Timothy A.,Karanewsky, Donald S.,Leibowitz, Mark D.,Liu, Sha,Mais, Dale A.,Mapes, Christopher M.,Montrose-Rafizadeh, Chahrzad,Ogilvie, Katheen M.,Reifel-Miller, Anne,Rungta, Deepa,Thompson, Anthony W.,Tyhonas, John S.,Boehm, Marcus F.
, p. 4087 - 4103 (2007/10/03)
Retinoid X receptor:peroxisome proliferative-activated receptor (RXR:PPAR) heterodimers play a critical role in the regulation of glucose (RXR/PPARγ) and lipid metabolism (RXR/PPARα). Previously, we described a concise structure-activity relationship stud
Synthesis of bridged medium-sized rings through the intramolecular Pauson-Khand reaction
Lovely, Carl J.,Seshadri, Hemalatha,Wayland, Brian R.,Cordes, A. Wallace
, p. 2607 - 2610 (2007/10/03)
(Equation presented) A series of aromatic enynes containing steric buttressing elements were prepared and evaluated in the NMO-mediated Pauson-Khand cyclization. O-Allyl systems led to the expected angularly fused products, whereas the O-butenyl and O-pentenyl derivatives afforded the unprecedented bridge systems.
Iodination of phenols and anilines with bis(sym-collidine)iodine(I) hexafluorophosphate
Brunel, Yves,Rousseau, Gerard
, p. 8217 - 8220 (2007/10/02)
Iodination of a wide range of phenols and anilines was achieved by the action of the title reagent in methylene chloride.
Oxidation of Phenols with Iodine in Alkaline Methanol
Omura, Kanji
, p. 3046 - 3050 (2007/10/02)
The use of iodine as an oxidizing agent for phenolic compounds has been explored.The reaction has been conducted in methanol containing such alkali as potassium hydroxide and, depending on the nature of the substituents and on the amount of iodine employed, leads to iodination, oxidation to give a stable phenoxy radical, oxidative dimerization, or benzylic oxidation.In general the reaction proceeds smoothly at room temperature, and under appropriate conditions yields of products are good to excellent.Oxidative dimerization of 2,4- and 2,6-di-tert-butylphenols invol-ves iodination followed by iodine-catalyzed dimerization.The oxidation of 4-methylphenols with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in methanol has been carried out for comparison.
