90725-40-9Relevant academic research and scientific papers
Ruthenium-catalyzed intramolecular arene C(sp2)-H amidation for synthesis of 3,4-dihydroquinolin-2(1 H)-ones
Au, Chi-Ming,Ling, Cho-Hon,Sun, Wenlong,Yu, Wing-Yiu
supporting information, p. 3310 - 3314 (2021/05/29)
We report the [Ru(p-cymene)(l-proline)Cl] ([Ru1])-catalyzed cyclization of 1,4,2-dioxazol-5-ones to form dihydroquinoline-2-ones in excellent yields with excellent regioselectivity via a formal intramolecular arene C(sp2)-H amidation. The reactions of the 2- and 4-substituted aryl dioxazolones proceeds initially through spirolactamization via electrophilic amidation at the arene site, which is para or ortho to the substituent. A Hammett correlation study showed that the spirolactamization is likely to occur by electrophilic nitrenoid attack at the arene, which is characterized by a negative ρ value of -0.73.
Visible-Light Induced C(sp2)?H Amidation with an Aryl–Alkyl σ-Bond Relocation via Redox-Neutral Radical–Polar Crossover
Chang, Sukbok,Jeong, Jiwoo,Jung, Hoimin,Keum, Hyeyun,Kim, Dongwook
supporting information, p. 25235 - 25240 (2021/10/25)
We report an approach for the intramolecular C(sp2)?H amidation of N-acyloxyamides under photoredox conditions to produce δ-benzolactams with an aryl-alkyl σ-bond relocation. Computational studies on the designed reductive single electron transfer strategy led us to identify N-[3,5-bis(trifluoromethyl)benzoyl] group as the most effective amidyl radical precursor. Upon the formation of an azaspirocyclic radical intermediate by the selective ipso-addition with outcompeting an ortho-attack, radical–polar crossover was then rationalized to lead to the rearomative ring-expansion with preferential C?C bond migration.
Palladium-Catalyzed Domino Allenamide Carbopalladation/Direct C-H Allylation of Heteroarenes: Synthesis of Primprinine and Papaverine Analogues
Hédouin, Jonathan,Schneider, Cédric,Gillaizeau, Isabelle,Hoarau, Christophe
supporting information, p. 6027 - 6032 (2018/10/05)
Palladium-catalyzed intramolecular carbopalladation onto allenamides completed by direct C-H allylation of heterocycles is studied. The domino construction/heteroarylation of isoquinolone process is first achieved. A general three-step one-pot strategy, i
Design, synthesis, and pharmacological evaluation of a novel series of hormone sensitive lipase inhibitor
Ogiyama, Tomoko,Yamaguchi, Mitsuhiro,Kurikawa, Nobuya,Honzumi, Shoko,Terayama, Koji,Nagaoka, Nobumi,Yamamoto, Yuka,Kimura, Takako,Sugiyama, Daisuke,Inoue, Shin-ichi
, (2017/10/05)
HSL inhibition is a promising approach to the treatment of dyslipidemia. As a result of re-optimization of lead compound 2, we identified novel compound 25a exhibiting potent inhibitory activity against HSL enzyme and cell with high selectivity for cholin
Rh(III)-Catalyzed meta-C-H Olefination Directed by a Nitrile Template
Xu, Hua-Jin,Lu, Yi,Farmer, Marcus E.,Wang, Huai-Wei,Zhao, Dan,Kang, Yan-Shang,Sun, Wei-Yin,Yu, Jin-Quan
supporting information, p. 2200 - 2203 (2017/02/23)
A range of Rh(III)-catalyzed ortho-C-H functionalizations have been developed; however, extension of this reactivity to remote C-H functionalizations through large-ring rhodacyclic intermediates has yet to be demonstrated. Herein we report the first examp
Photoinduced, Copper-Catalyzed Decarboxylative C-N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement
Zhao, Wei,Wurz, Ryan P.,Peters, Jonas C.,Fu, Gregory C.
supporting information, p. 12153 - 12156 (2017/09/12)
The Curtius rearrangement is a classic, powerful method for converting carboxylic acids into protected amines, but its widespread use is impeded by safety issues (the need to handle azides). We have developed an alternative to the Curtius rearrangement that employs a copper catalyst in combination with blue-LED irradiation to achieve the decarboxylative coupling of aliphatic carboxylic acid derivatives (specifically, readily available N-hydroxyphthalimide esters) to afford protected amines under mild conditions. This C-N bond-forming process is compatible with a wide array of functional groups, including an alcohol, aldehyde, epoxide, indole, nitroalkane, and sulfide. Control reactions and mechanistic studies are consistent with the hypothesis that copper species are engaged in both the photochemistry and the key bond-forming step, which occurs through out-of-cage coupling of an alkyl radical.
Metallocenes and catalyst compositions derived therefrom
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Page/Page column 51, (2016/02/26)
This invention relates to a novel group 2, 3 or 4 transition metal metallocene catalyst compound that is asymmetric having two non-identical indenyl ligands with substitution at R2 having a branched or unbranched C1-C20 alkyl group substituted with a cyclic group or a cyclic group, R8 is an alkyl group and R4 and R10 are substituted phenyl groups.
Synthesis of Alkyl-Substituted Pyridines by Directed Pd(II)-Catalyzed C-H Activation of Alkanoic Amides
Hu, Peng,Bach, Thorsten
supporting information, p. 2853 - 2857 (2015/12/18)
A general alkylation protocol for substituted iodopyridines was developed (32 examples, 44-97% yield). The reaction is based on the Pd(II)-catalyzed C-H activation of 8-aminoquinoline-derived alkanoic amides and it employs a catalyst cocktail of Pd(OAc)2 (10 mol%), NaI (30 mol%), and (BuO)2POOH (20 mol%), with Ag2CO3 as base.
Synthesis and reactivity of ortho-palladated 3-phenylpropanamides. Insertion of CO, XyNC, and alkynes into the Pd-C bond. Synthesis of seven-and nine-membered palladacycles and benzazepine-and benzazonine-based heterocycles
Frutos-Pedreno, Roberto,Gonzalez-Herrero, Pablo,Vicente, Jose,Jones, Peter G.
supporting information, p. 1892 - 1904 (2013/05/08)
Aryl palladium complexes [Pd{C6H4(CH 2)2C(O)NRR′)-2}I(tmeda)] [NRR′ = NH 2 (1a), NHMe (1b), NMe2 (1c); tmeda = N,N,N′, N′-tetramethylethylenediamine] are prepared by oxidative addition of t
COMPOSITIONS COMPRISING AND METHODS FOR FORMING FUNCTIONALIZED CARBON-BASED NANOSTRUCTURES
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Page/Page column 18-19, (2012/05/20)
The present invention generally relates to compositions comprising and methods for forming functionalized carbon-based nanostructures.
