15310-02-8Relevant academic research and scientific papers
Aniline-Type Hypervalent Iodine(III) for Intramolecular Cyclization via C?H Bond Abstraction of Hydrocarbons Containing N- and O-Nucleophiles
Nishiguchi, Yuna,Moriyama, Katsuhiko
supporting information, p. 3354 - 3358 (2021/05/17)
We developed a method for the preparation of (diacetoxyiodo)-2-(N-alkylamido)benzene as an aniline-type hypervalent iodine(III). We also achieved direct cyclizations via C?H bond abstraction, such as the Hofmann-L?ffler-Freytag reaction, a direct amination, and a direct lactonization, using the aniline-type hypervalent iodine(III) to obtain corresponding products in high yields. (Figure presented.).
Dibrominative Spirocyclization of 2-Butynolyl Anilides: Synthesis of gem-Dibromospirocyclic Benzo[ d][1,3]oxazines and Their Application in the Synthesis of 4 H-Furo[3,2- b]indoles
Chaisan, Nattawadee,Ruengsangtongkul, Sureeporn,Tummatorn, Jumreang,Ruchirawat, Somsak,Chainok, Kittipong,Thongsornkleeb, Charnsak
, p. 4671 - 4698 (2021/04/06)
The combination of catalytic aqueous hydrochloric acid (HCl) and N-bromosuccinimide (NBS) generated electrophilic bromine monochloride (BrCl), which readily induced spiroannulation of 2-alkynolyl anilides (n = 1-3) to form gem-dibromospirocyclic benzo[d][
Novel and efficient heterogeneous polymer supported copper catalyst for synthesis of 2-substituted Benzoxazoles from 2-Haloanilides
Saranya, Thachora Venu,Sruthi, Pambingal Rajan,Raj, Veena,Anas, Saithalavi
supporting information, (2021/02/27)
A novel polymer supported copper complex is prepared by the immobilization of copper iodide on chemically modified polyacrylonitrile and its application in heterogeneous catalysis is described. The catalyst was prepared by easy method via synthetic modification of Polyacrylonitrile (PAN) using ethylene diamine followed by the complexation with CuI. After characterization, this complex was explored as a green and efficient heterogeneous catalyst for the synthesis of 2-benzoxazoles from 2-haloanilides. The reaction was performed without adding additional ligand and the catalyst shows activity over a broad range of substrates with quantitative product yields. The catalyst was easily recovered by simple filtration and reused successfully for further cycle.
Gold-catalyzed oxidative cyclization of amide-alkynes: access to functionalized γ-lactams
Zheng, Yi,Zhang, Ting-Ting,Shen, Wen-Bo
supporting information, p. 9688 - 9691 (2021/12/01)
An efficient gold-catalyzed oxidative cyclization of amide-alkynes is developed. A series of functionalized γ-lactams are easily accessed by employing this strategy. The tandem reaction proceeds through alkyne oxidation, carbene/alkyne metathesis, and donor/donor carbene oxidation.
Efficient Pd-Catalyzed Hydrodehalogenation of o -Haloanilides in Water
Gao, Hui,Li, Minxin,Mao, Zewei,Rao, Gaoxiong,Tang, Yanling
supporting information, p. 1121 - 1125 (2020/07/03)
In the present work, we have developed a practical methodology for the hydrodehalogenation of o -haloanilides using PdCl 2at 100 °C under mild conditions in water. The catalytic system could selectively dehalogenate both aryl chloride and aryl bromide and exhibit a broad functional group tolerance.
Hydroarylation of Arenes via Reductive Radical-Polar Crossover
Flynn, Autumn R.,Mcdaniel, Kelly A.,Hughes, Meredith E.,Vogt, David B.,Jui, Nathan T.
supporting information, p. 9163 - 9168 (2020/07/10)
A photocatalytic system for the dearomative hydroarylation of benzene derivatives has been developed. Using a combination of an organic photoredox catalyst and an amine reductant, this process operates through a reductive radical-polar crossover mechanism where aryl halide reduction triggers a regioselective radical cyclization event, followed by anion formation and quenching to produce a range of complex spirocyclic cyclohexadienes. This light-driven protocol functions at room temperature in a green solvent system (aq. MeCN) without the need for precious metal-based catalysts or reagents or the generation of stoichiometric metal byproducts.
Lewis Acid Catalyzed Atom-Economic Synthesis of C2-Substituted Indoles from o-Amido Alkynols
Garkhedkar, Amol Milind,Gore, Babasaheb Sopan,Hu, Wan-Ping,Wang, Jeh-Jeng
supporting information, p. 3531 - 3536 (2020/04/20)
Herein we have disclosed a Zn(OTf)2 catalyzed synthesis of C2-alkyl substituted indole derivatives via unprecedented carbonyl group migration from o-amido alkynols. The key features of this protocol involve N,O-carbonyl group migration, broad s
Synthesis of Aminated Phenanthridinones via Palladium/Norbornene Catalysis
Abel-Snape, Xavier,Whyte, Andrew,Lautens, Mark
supporting information, p. 7920 - 7925 (2020/11/02)
An ortho-amination, ipso-C-H arylation mediated by palladium/norbornene cooperative catalysis is reported. This reaction proceeds through a sequential intermolecular C-N bond formation process followed by intramolecular C-H activation of a tethered arene. The products, aminated phenanthridinones, were generated in moderate to good yields. This method is also applicable to the formation of dibenzazepinones.
Nickel-Catalyzed trans-Carboamination across Internal Alkynes to Access Multifunctionalized Indoles
Tambe, Shrikant D.,Iqbal, Naeem,Cho, Eun Jin
supporting information, p. 8550 - 8554 (2020/11/12)
A Ni-catalyzed reaction was developed for the synthesis of multifunctionalized indoles. The reaction proceeded through oxidative cyclization of the Ni(0)/P^N complex with an enyne system, 2-alkynyl anilinoacrylate, to provide a nickelacycle intermediate. The trans-carboamination around the internal alkyne was achieved by syn/anti-rotation of the Ni-carbenoid intermediate formed by C-N bond cleavage of the nickelacycle, and 3-alkenylated indoles were formed by C-N bond-forming reductive elimination. Notably, the synthesized indoles could be successfully transformed to functionalized carbazoles.
Acyl Cyanides as Bifunctional Reagent: Application in Copper-Catalyzed Cyanoamidation and Cyanoesterification Reaction
Chen, Zhengwang,Wen, Xiaowei,Zheng, Weiping,He, Ruolan,Chen, Dou,Cao, Dingsheng,Long, Lipeng,Ye, Min
, p. 5691 - 5701 (2020/04/10)
Cu-catalyzed domino decyanation and cyanation reaction of acyl cyanides with amines or alcohols have been developed. The cyano sources were generated in situ via C-CN cleavage yielding the corresponding cyano substituted amides or esters in moderate to excellent yields. This approach features a cheap copper catalyst, domino decyanation and cyanation reaction, readily available starting materials, broad substrate scope, operational simplicity, and the potential for further transformation of the cyano group.
