1846-18-0Relevant academic research and scientific papers
Radical hydroalkylation and hydroacylation of alkenes by the use of benzothiazoline under thermal conditions
Akiyama, Takahiko,Uchikura, Tatsuhiro,Toda, Mitsuhiro,Mouri, Toshiki,Fujii, Tatsuya,Moriyama, Kaworuko,Ibanez, Ignacio
, p. 12715 - 12723 (2020)
The hydroalkylation and hydroacylation of electrondeficient alkenes proceeded smoothly by using benzothiazoline derivatives as radical-transfer reagents under thermal conditions without light irradiation or any additive. Both benzyl and benzoyl moieties were transferred efficiently.
Direct Cyclopropanation of α-Cyano β-Aryl Alkanes by Light-Mediated Single Electron Transfer Between Donor–Acceptor Pairs
Li, Jing,Lear, Martin J.,Hayashi, Yujiro
, p. 5901 - 5905 (2021/03/09)
Cyclopropanes are traditionally prepared by the formal [2+1] addition of carbene or radical based C1 units to alkenes. In contrast, the one-pot intermolecular cyclopropanation of alkanes by redox active C1 units has remained unrealised. Herein, we achieve
C(sp3)-H functionalizations of light hydrocarbons using decatungstate photocatalysis in flow
Deng, Yuchao,Fagnoni, Maurizio,Guthrie, Duncan,Laudadio, Gabriele,No?l, Timothy,Nun?, Manuel,Ravelli, Davide,Sun, Yuhan,Wal, Klaas Van Der
, p. 92 - 96 (2020/09/03)
Direct activation of gaseous hydrocarbons remains a major challenge for the chemistry community. Because of the intrinsic inertness of these compounds, harsh reaction conditions are typically required to enable C(sp3)-H bond cleavage, barring potential applications in synthetic organic chemistry. Here, we report a general and mild strategy to activate C(sp3)-H bonds in methane, ethane, propane, and isobutane through hydrogen atom transfer using inexpensive decatungstate as photocatalyst at room temperature. The corresponding carbon-centered radicals can be effectively trapped by a variety of Michael acceptors, leading to the corresponding hydroalkylated adducts in good isolated yields and high selectivity (38 examples).
Benzothiazolines as radical transfer reagents: Hydroalkylation and hydroacylation of alkenes by radical generation under photoirradiation conditions
Uchikura, Tatsuhiro,Moriyama, Kaworuko,Toda, Mitsuhiro,Mouri, Toshiki,Ibá?ez, Ignacio,Akiyama, Takahiko
supporting information, p. 11171 - 11174 (2019/09/30)
Novel radical transfer reagents under photoirradiation conditions were developed by the use of benzothiazoline derivatives. These reagents enabled both hydroalkylation and hydroacylation of alkenes under neutral conditions at ambient temperature without a
One-pot synthesis of malononitriles by free radical reactions of ylidenemalononitrile with Et3B and iodoalkane in a water-ether biphase medium
Tu, Zhijay,Lin, Chunchi,Jang, Yaochung,Jang, Yeong-Jiunn,Ko, Shengkai,Fang, Hulin,Liu, Ju-Tsung,Yao, Ching-Fa
, p. 6133 - 6137 (2007/10/03)
The one-pot synthesis of malononitrile derivatives 4, 6, and 7 in moderate to high yields by the reaction of ylidenemalononitriles 3, prepared in situ from carbonyl compounds 1 and malononitrile 2 in the presence of ammonium acetate in aqueous solution at
Photochemistry of some trialkylsilyloxybenzylidenemalonic acid derivatives. C-Si bond fragmentation in a polarized excited state
Courtney, Michael C.,Mella, Mariella,Albini, Angelo
, p. 1105 - 1110 (2007/10/03)
Photolysis of 3-(tert-butyldimethylsilyloxyphenyl)methylenemalonodinitrile (2) in a polar medium leads to C-Si cleavage via the polarized singlet excited state.The thus formed tert-butyl radicals diffuse out of cage and are trapped by further molecules of
tert-Butylation of α,β-unsaturated nitriles by tert-butylmercury halides in the presence of iodide ion
Russell, Glen A.,Chen, Ping,Yao,Kim
, p. 5967 - 5972 (2007/10/02)
Iodide ion promotes the free radical addition of t-BuHgI to acrylonitrile to form t-BuCH2CH(CN)HgI. A facile reaction of the adduct 1-cyanoalkyl radical with t-BuHgI2- is indicated. Further promotion is observed in the pre
Electro-organic Reactions. Part 26. The Cathodic Reduction of Dicyanoethylene Derivatives; Competition between Hydrogenation and Hydrodimerisation
Clarke, Norman C.,Runciman, Peter J. I.,Utley, James H. P.,Landquist, Justus K.
, p. 435 - 440 (2007/10/02)
Dicyanoethylene derivatives, and related compounds, undergo smooth cathodic reduction to give the products of hydrogenation (2 F mol-1), hydrodimerisation (1 F mol-1), or a mixture of both.The product distribution depends crucially u
