876337-56-3Relevant academic research and scientific papers
Nickel-Catalyzed Mizoroki-Heck/Amination Cascade Reactions of o-Dihaloarenes with Allylamines: Synthesis of Indoles
Chen, Xu,Lin, Jin,Wang, Biao,Tian, Xu
supporting information, p. 7704 - 7708 (2020/10/12)
An efficient Mizoroki-Heck/amination cascade reaction of o-dihaloarenes with allylamines has been developed using nickel and IPr carbene ligand as catalyst. This protocol enables the synthesis of a broad range of substituted indoles by a cascade process, from readily available starting materials. Mechanistic studies suggest that the Mizoroki-Heck reaction occurred first under IPr-nickel catalysis.
A Newly Designed Carbohydrate-Derived Alkylamine Promotes Ullmann Type C-N Coupling Catalyzed by Copper in Water
Zhou, Guoquan,Chen, Wen,Zhang, Shihui,Liu, Xuemin,Yang, Zehui,Ge, Xin,Fan, Hua-Jun
supporting information, p. 193 - 198 (2019/01/14)
A green and biodegradable carbohydrate-derived alkylamine was designed and employed as ligand for Ullmann type C-N coupling catalyzed by copper in water. The coupling of aryl iodide and N-nucleophiles were examined and moderate to excellent yields were obtained. In addition, the in-water coupling strategy was expanded successfully to the reaction of indoles with 4-iodoanisole. By measuring the solubility, it is speculated that carbohydrate-derived alkylamine plays the role of chelating copper and promoting the dissolution of 4-iodoanisole in water. Remarkably, this methodology was environmentally friendly and economical because of the use of aqueous media in place of organic solvents.
A designed bi-functional sugar-based surfactant: Micellar catalysis for C-X coupling reaction in water
Ge, Xin,Zhang, Shihui,Chen, Xinzhi,Liu, Xuemin,Qian, Chao
supporting information, p. 2771 - 2776 (2019/06/13)
A bi-functional sugar-based surfactant ALA14 was designed as the ligand and micelle constructor and demonstrated to promote the copper-catalyzed C-X coupling reaction in water. The nature of this micelle, formed by sugar-based surfactants, was investigated with CMC, DLS, and TEM, by which encapsulation and aggregation of the substrates in micelles were verified. Additionally, it was addressed by 1H-NMR analysis that the enrichment position of the substrates is in the lipophilic alkyl chain. Finally, moderate to excellent yields of the aimed products were obtained in this work. This remarkably simple strategy expanded the scope of C-X coupling reaction in water; most notably, both water and ALA14 can be recycled and reused.
Br?nsted Acid-Catalyzed Synthesis of N-Arylindoles from 2-Vinylanilines and Quinones
Zhang, Han-Ming,Gao, Zhong-Hua,Yi, Liang,Ye, Song
, p. 2671 - 2674 (2016/10/11)
In the presence of a quinone, Br?nsted acid-catalyzed intramolecular C?N bond formation of o-vinylanilines by electrophilic cyclization was developed, giving the corresponding N-arylindoles in good to high yields. The reaction worked well for o-vinylanilines with terminal and internal C=C double bonds.
Indole-based allosteric inhibitors of HIV-1 integrase
Patel, Pratiq A.,Kvaratskhelia, Nina,Mansour, Yara,Antwi, Janet,Feng, Lei,Koneru, Pratibha,Kobe, Mathew J.,Jena, Nivedita,Shi, Guqin,Mohamed, Mosaad S.,Li, Chenglong,Kessl, Jacques J.,Fuchs, James R.
supporting information, p. 4748 - 4752 (2016/09/13)
Employing a scaffold hopping approach, a series of allosteric HIV-1 integrase (IN) inhibitors (ALLINIs) have been synthesized based on an indole scaffold. These compounds incorporate the key elements utilized in quinoline-based ALLINIs for binding to the IN dimer interface at the principal LEDGF/p75 binding pocket. The most potent of these compounds displayed good activity in the LEDGF/p75 dependent integration assay (IC50?=?4.5?μM) and, as predicted based on the geometry of the five- versus six-membered ring, retained activity against the A128T IN mutant that confers resistance to many quinoline-based ALLINIs.
Copper-catalyzed synthesis of N-aryl and N-sulfonyl indoles from 2-vinylanilines with O2 as terminal oxidant and TEMPO as cocatalyst
Liwosz, Timothy W.,Chemler, Sherry R.
, p. 335 - 339 (2015/02/19)
A copper-catalyzed intramolecular alkene oxidative amination that utilizes TEMPO as cocatalyst and O2 as the terminal oxidant has been developed. The method furnishes N-aryl and N-sulfonyl indoles from N-aryl and N-sulfonyl 2-vinylanilines, res
SBA-15-functionalized melamine-pyridine group-supported palladium(0) as an efficient heterogeneous and recyclable nanocatalyst for N-arylation of indoles through Ullmann-type coupling reactions
Veisi, Hojat,Poor Heravi, Mohammad Reza,Hamelian, Mona
, p. 334 - 337 (2015/04/27)
SBA-15-functionalized melamine-pyridine group-supported palladium(0) was found to serve as a heterogeneous and recyclable nanocatalyst for N-arylation of indoles with aryl iodides under a low catalyst loading (0.3mol% of Pd) through Ullmann-type C￡N coupling reactions. A variety of aryl iodides could be aminated to provide the N-arylated products in good to excellent yields without the need of an inert atmosphere. Also, this catalyst was found to be an efficient system for the N-arylation of other nitrogen-containing heterocycles with aryl iodides. The heterogeneous palladium catalyst could be recovered by simple filtration of the reaction solution and reused for six cycles without significant loss in its activity.
Palladium nanoparticles supported on modified single-walled carbon nanotubes: A heterogeneous and reusable catalyst in the Ullmann-type N-arylation of imidazoles and indoles
Veisi, Hojat,Morakabati, Nekoo
, p. 2901 - 2907 (2015/04/14)
Air- and moisture-stable and recyclable palladium nanoparticles supported on modified single-walled carbon nanotubes (SWCNT-Met/Pd) behave as very efficient heterogeneous catalysts in the Ullmann coupling of imidazoles and indoles with aryl iodides to afford the corresponding C-N coupling reactions under aerobic conditions. These cross coupled products were produced in excellent yields at low palladium loading (～0.2 mol%) and the heterogeneous catalyst can be readily recovered by simple filtration and reused five times without a noticeable loss in its catalytic activity.
An efficient, mild and selective Ullmann-type N-arylation of indoles catalysed by Pd immobilized on amidoxime-functionalized mesoporous SBA-15 as heterogeneous and recyclable nanocatalyst
Ghorbani-Vaghei, Ramin,Hemmati, Saba,Hamelian, Mona,Veisi, Hojat
, p. 195 - 199 (2015/03/30)
A wide range of N-arylated indoles were selectively synthesized through intermolecular C(aryl)-N bond formation from the corresponding aryl iodides and indoles through Ullmann-type coupling reactions in the presence of a catalytic amount of Pd immobilized on amidoxime-functionalized mesoporous SBA-15 (SBA-15/AO/Pd(0)) under mild reaction conditions. These cross-coupled products were obtained in excellent yields under mild conditions at extremely low palladium loading (ca 0.3 mol%), and the heterogeneous catalyst can be readily recovered by simple filtration and reused seven times with loss in its activity.
Aqueous copper-catalyzed N-arylation of indoles: The surfactant strategy
Liu, Songbai,Zhou, Jiahui
supporting information, p. 2537 - 2540 (2013/09/24)
Surfactants have long been underestimated in synthetic organic chemistry despite their great potential in promoting solubility, reactivity and selectivity in metal-mediated cross-couplings. In this study the strategy of surfactant promotion was exemplified in copper-catalyzed N-arylation of indoles in water. The different effects of surfactants during the coupling reaction were first explored. The superior promoting effect of the natural zwitterionic surfactant, betaine, was found and attributed to the capability of the formed complex to stabilize the copper intermediate in the catalytic transformation and facilitate transportation of the reactants. The concept of surfactant promotion through complexation is valuable in metal-mediated cross-couplings. This method also exhibited good recycling ability. This study will greatly facilitate exploration of surfactant promotion in metal-mediated cross-couplings.
