4119-41-9Relevant academic research and scientific papers
Chromenes involving a two-photon absorbing moiety: Photochromism via intramolecular resonance energy transfer
Bekere, Laura,Lokshin, Vladimir,Sigalov, Mark,Gvishi, Raz,Zhao, Peng,Hagan, David J.,Van Stryland, Eric W.,Khodorkovsky, Vladimir
, p. 1143 - 1148 (2016)
New derivatives involving the photochromic 2H-benzo[h]chromene moieties covalently linked to the 2,7-bis(carbazolyl)fluorene-derived two-photon absorbing moiety were designed to enable the possibility of resonance energy transfer from the fluorene donor to the photochromic acceptor. The longest wavelength absorption of the photochromic acceptors overlaps with the fluorescence band of the two-photon absorbing donor and the distance between the both moieties is about 5-7 ?. Rapid coloration of colorless solutions was observed upon one- and two-photon absorption.
Iridium-Catalyzed Hydroiodination and Formal Hydroamination of Olefins with N-Iodo Reagents and Molecular Hydrogen: An Umpolung Strategy
Wen, Jialin,Yang, Huaxin,Zhang, Xumu,Zhang, Zhihan,Zhou, Yang
supporting information, p. 1842 - 1847 (2022/03/14)
We herein report a convenient method to convert olefins to organic iodides and amines using an Ir/ZhaoPhos catalyst, molecular hydrogen, and an electrophilic iodine(I) reagent. High yields and regioselectivities were obtained under mild conditions. In addition, basic workup with potassium carbonate leads to C-N products. Control experiments and DFT calculations tentatively excluded the pathway involving the in situ formation of HI. Instead, a catalytic cycle involving the hydrogenation of the haliranium ion intermediate was proposed.
One-Pot Deoxygenation and Substitution of Alcohols Mediated by Sulfuryl Fluoride
Epifanov, Maxim,Mo, Jia Yi,Dubois, Rudy,Yu, Hao,Sammis, Glenn M.
, p. 3768 - 3777 (2021/03/01)
Sulfuryl fluoride is a valuable reagent for the one-pot activation and derivatization of aliphatic alcohols, but the highly reactive alkyl fluorosulfate intermediates limit both the types of reactions that can be accessed as well as the scope. Herein, we report the SO2F2-mediated alcohol substitution and deoxygenation method that relies on the conversion of fluorosulfates to alkyl halide intermediates. This strategy allows the expansion of SO2F2-mediated one-pot processes to include radical reactions, where the alkyl halides can also be exploited in the one-pot deoxygenation of primary alcohols under mild conditions (52-95% yield). This strategy can also enhance the scope of substitutions to nucleophiles that are previously incompatible with one-pot SO2F2-mediated alcohol activation and enables substitution of primary and secondary alcohols in 54-95% yield. Chiral secondary alcohols undergo a highly stereospecific (90-98% ee) double nucleophilic displacement with an overall retention of configuration.
Copper-Catalyzed Alkoxycarbonylation of Alkyl Iodides for the Synthesis of Aliphatic Esters: Hydrogen Makes the Difference
Geng, Hui-Qing,Wu, Xiao-Feng
supporting information, p. 8062 - 8066 (2021/10/25)
A copper-catalyzed alkoxycarbonylation transformation of unactivated alkyl iodides has been developed. Various alkyl iodides can be converted into the corresponding tert-butyl esters in good yields. NaOtBu acts as both a nucleophile and a base. Moreover, other types of aliphatic esters can also be obtained in moderated yields if extra alcohols are added. Both primary and secondary alkyl alcohols can react successfully.
Nickel-Catalyzed Formal Aminocarbonylation of Unactivated Alkyl Iodides with Isocyanides
Chen, Yifeng,Huang, Wenyi,Qu, Jingping,Shrestha, Mohini,Wang, Yun,Weng, Yangyang
, p. 3245 - 3250 (2020/04/21)
Herein, we disclose a Ni-catalyzed formal aminocarbonylation of primary and secondary unactivated aliphatic iodides with isocyanides to afford alkyl amide, which proceeds via the selective monomigratory insertion of isocyanides with alkyl iodides, subsequent β-hydride elimination, and hydrolysis process. The reaction features wide functional group tolerance under mild conditions. Additionally, the selective, one-pot hydrolysis of reaction mixture under acid conditions allows for expedient synthesis of the corresponding alkyl carboxylic acid.
Cuprous complex containing diphospho-ortho-carborane ligand as well as preparation method and application thereof (by machine translation)
-
Paragraph 0047-0049; 0052-0056, (2020/05/02)
The method comprises the following steps, adding :1) solution to the ortho-carborane solution n - BuLi, reacting, at room temperature for 30 - 60min;2), adding, and reacting 1 - 3h;3) with high yield CuI, of the monovalent copper complex to react alcohol and iodide to synthesize the iodo-hydrocarbon 3 - 6h, and synthesizing the iodo-hydrocarbon; through post-treatment at room temperature for synthesizing the iodo-copper complex, by the following steps: reacting the alcohol with the iodide at room temperature and carrying out post-treatment to obtain the monovalent copper complex . The preparation method comprises the following steps: catalyzing alcohol and iodide to react with the iodide, to synthesize the iodo- hydrocarbyl complex; and the method comprises the following steps: catalyzing alcohol and iodide to react. (by machine translation)
Ligand Free Palladium-Catalyzed Synthesis of α-Trifluoromethylacrylic Acids and Related Acrylates by Three-Component Reaction
Bouillon, Jean-Philippe,Couve-Bonnaire, Samuel,Pannecoucke, Xavier,Xiao, Pan
supporting information, p. 949 - 954 (2020/01/28)
Aryl iodides and 2-(trifluoromethyl)acrylic acid reacted together in ligand-free Mizoroki-Heck reaction furnishing a quick and efficient access to highly valuable α-trifluoromethylacrylic acids. The useful transformation was independent with regard to the electronic nature of the aryl group substituent. A three-component one-pot version was also developed to give diverse substituted acrylates. The versatility of α-trifluoromethylacrylic acids was demonstrated by quick access to 3-CF3-coumarins as well as fluorinated analogues of therapeutic or cosmetic agents. Finally, we proposed a catalytic cycle based on the silver carboxylate salt, identified as a key intermediate in the reaction. (Figure presented.).
Alkyl Group Migration in Ni-Catalyzed Conjunctive Coupling with C(sp3) Electrophiles: Reaction Development and Application to Targets of Interest
Koo, Seung Moh,Vendola, Alex J.,Momm, Sarah Noemi,Morken, James P.
supporting information, p. 666 - 669 (2020/01/31)
A catalytic conjunctive cross-coupling reaction is developed that allows the construction of chiral organoboronic esters from alkylboron ate complexes and alkyl iodide electrophiles. The process occurs most efficiently with a Ni/Pybox-comprised catalyst a
A click-based modular approach to introduction of peroxides onto molecules and nanostructures
Dussault, Patrick H.,Horn, Alissa
, p. 44408 - 44429 (2020/12/28)
Copper-promoted azide/alkyne cycloadditions (CuAAC) are explored as a tool for modular introduction of peroxides onto molecules and nanomaterials. Dialkyl peroxide-substituted alkynes undergo Cu(i)-promoted reaction with azides in either organic or biphas
Migratory Hydrogenation of Terminal Alkynes by Base/Cobalt Relay Catalysis
Liu, Bingxue,Liu, Qiang,Liu, Xufang
supporting information, p. 6750 - 6755 (2020/03/13)
Migratory functionalization of alkenes has emerged as a powerful strategy to achieve functionalization at a distal position to the original reactive site on a hydrocarbon chain. However, an analogous protocol for alkyne substrates is yet to be developed. Herein, a base and cobalt relay catalytic process for the selective synthesis of (Z)-2-alkenes and conjugated E alkenes by migratory hydrogenation of terminal alkynes is disclosed. Mechanistic studies support a relay catalytic process involving a sequential base-catalyzed isomerization of terminal alkynes and cobalt-catalyzed hydrogenation of either 2-alkynes or conjugated diene intermediates. Notably, this practical non-noble metal catalytic system enables efficient control of the chemo-, regio-, and stereoselectivity of this transformation.
