2192-34-9Relevant academic research and scientific papers
Transition-Metal- A nd Light-Free Directed Amination of Remote Unactivated C(sp3)-H Bonds of Alcohols
Kurandina, Daria,Yadagiri, Dongari,Rivas, Monica,Kavun, Aleksei,Chuentragool, Padon,Hayama, Keiichi,Gevorgyan, Vladimir
supporting information, p. 8104 - 8109 (2019/06/13)
Due to the great value of amino alcohols, new methods for their synthesis are in high demand. Abundant aliphatic alcohols represent the ideal feedstock for the method development toward this important motif. To date, transition-metal-catalyzed approaches for the directed remote amination of alcohols have been well established. Yet, they have certain disadvantages such as the use of expensive catalysts and limited scope. Very recently, transition-metal-free visible-light-induced radical approaches have emerged as new powerful tools for directed remote amination of alcohols. Relying on 1,5-HAT reactivity, these methods are limited to β-or δ- A mination only. Herein, we report a novel transitionmetal- A nd visible-light-free room-temperature radical approach for remote β-, γ-, and δ-C(sp3)-N bond formation in aliphatic alcohols using mild basic conditions and readily available diazonium salt reagents.
Preparation of N-Arylquinazolinium Salts via a Cascade Approach
Ramanathan, Mani,Wan, Jing,Liu, Shiuh-Tzung
, p. 7459 - 7467 (2019/06/14)
An easy manipulation method for the preparation of N-arylquinazolinium salts is described from readily available aryldiazonium salts, nitriles, and 2-aminoarylketones in a one-pot operation. This method relies on the in situ generation of the N-arylnitrilium intermediate from the reaction of aryldiazonium salt with nitrile, which undergoes amination/cascade cyclization/aromatization, leading to N-arylquinazolinium salts in excellent yields. Nucleophilic addition of alkoxide to these N-arylquinazolinium salts provides functionalized dihydro-N-arylquinazoline.
Visible-Light-Mediated Hydroxycarbonylation of Diazonium Salts
Gosset, Cyrille,Pellegrini, Sylvain,Jooris, Romain,Bousquet, Till,Pelinski, Lydie
supporting information, p. 3401 - 3405 (2018/08/06)
A visible light-promoted catalytic photoredox hydroxycarbonylation was achieved on aryl diazonium salts whether preformed or generated in situ from the corresponding anilines. This strategy allows a straightforward access to a variety of carboxylic acids under mild conditions. (Figure presented.).
Copper-Catalyzed Arylsulfonylation and Cyclizative Carbonation of N-(Arylsulfonyl)acrylamides Involving Desulfonative Arrangement toward Sulfonated Oxindoles
Wang, Hepan,Sun, Song,Cheng, Jiang
supporting information, p. 5844 - 5847 (2017/11/10)
Sulfonated oxindoles are accessed by a Cu(OAc)2-catalyzed three-component reaction of N-(arylsulfonyl)acrylamides, DABSO, and aryldiazonium tetrafluoroborates. This transformation is triggered by the formation of arylsulfonyl radicals in situ from the reaction of aryldiazonium tetrafluoroborates and DABSO. Afterward, the sequential radical addition, radical cyclization, and desulfonylative 1,4-aryl migration take place to provide the final product by the formation of four new bonds in one pot. This procedure shows good functional group tolerance.
