34231-76-0Relevant academic research and scientific papers
Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts
Zhao, Yue,Yu, Congjun,Liang, Wenjing,Patureau, Frederic W.
, p. 6232 - 6236 (2021/08/23)
The construction of (hetero)biaryls, which are ubiquitous scaffolds among medical substances, functional materials, and agrochemicals, constitutes a key application of cross-coupling methods. However, these usually require multiple synthetic steps. Herein, we report a simple photoinduced and catalyst-free C-H/C-H (hetero)arylation cross-coupling through aryl thianthrenium salts, which are formed site-selectively by direct C-H functionalization. The key to this approach is the UV-light, which can disrupt the C-S bond to form thianthrene radical cations and aryl radicals.
Redox reactions of small organic molecules using ball milling and piezoelectric materials
Kubota, Koji,Pang, Yadong,Miura, Akira,Ito, Hajime
, p. 1500 - 1504 (2020/01/08)
Over the past decade, photoredox catalysis has harnessed light energy to accelerate bond-forming reactions. We postulated that a complementary method for the redox-activation of small organic molecules in response to applied mechanical energy could be dev
Synthesis of 2,5-Disubstituted Furans from Sc(OTf)3 Catalyzed Reaction of Aryl Oxiranediesters with γ-Hydroxyenones
Mondal, Keshab,Pan, Subhas Chandra
, p. 4415 - 4421 (2017/04/27)
A convenient synthesis of 2,5-disubstituted furan was developed by employing donor-acceptor oxiranes in a new reaction with γ-hydroxyenones. Sc(OTf)3 was found to be the best catalyst, and 2,5-disubstituted furans are obtained in moderate to good yields under mild reaction conditions. The scope of the reaction is quite decent, allowing for the synthesis of disubstituted furans having aryl and heteroaromatic groups.
Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C?O and C?N Bond Activation
Yue, Huifeng,Guo, Lin,Lee, Shao-Chi,Liu, Xiangqian,Rueping, Magnus
supporting information, p. 3972 - 3976 (2017/03/27)
An inexpensive nickel(II) catalyst and a hydrosilane were used for the efficient reductive defunctionalization of aryl and heteroaryl esters through a decarbonylative pathway. This versatile method could be used for the removal of ester and amide functional groups from various organic molecules. Moreover, a scale-up experiment and a synthetic application based on the use of a removable carboxylic acid directing group highlight the usefulness of this reaction.
Wavelength Selective Generation of Aryl Radicals and Aryl Cations for Metal-Free Photoarylations
Crespi, Stefano,Protti, Stefano,Fagnoni, Maurizio
, p. 9612 - 9619 (2016/11/02)
Photochemical reactions have become an important tool for organic chemists. Visible (solar) light can be conveniently adopted, however, only when using colored organic compounds or in photocatalyzed processes induced by visible light absorbing photocatalysts. Herein we demonstrate that a photolabile, colored moiety could be incorporated in a colorless organic compound with the aim of generating highly reactive intermediates upon exposure to visible (solar) light. Arylazo sulfones, colored thermally stable derivatives of aryl diazonium salts, were used as valuable substrates for the photoinduced metal-free synthesis of (hetero)biaryls with no need of a (photo)catalyst or of other additives to promote the reaction. Noteworthy, selective generation of aryl radicals and aryl cations can be attained at will by varying the irradiation conditions (visible light for the former and UVA light for the latter).
1,4-Difluoro-2,5-dimethoxybenzene as a precursor for iterative double benzyne-furan Diels-Alder reactions
Morton, Gillian E.,Barrett, Anthony G. M.
, p. 3525 - 3529 (2007/10/03)
(Chemical Equation Presented) The use of 1,4-difluoro-2,5-dimethoxybenzene as a novel precursor for iterative two-directional benzyne-furan Diels-Alder reactions, using a range of 2- and 3-substituted furans, is reported. Substituted oxabenzonorbornadiene
