6144-04-3Relevant articles and documents
Noble-metal-free deoxygenation of epoxides: Titanium dioxide as a photocatalytically regenerable electron-transfer catalyst
Shiraishi, Yasuhiro,Hirakawa, Hiroaki,Togawa, Yoshiki,Hirai, Takayuki
, p. 1642 - 1649 (2014)
Catalytic deoxygenation of epoxides into the corresponding alkenes is a very important reaction in organic synthesis. Early reported systems, however, require noble metals, high reaction temperatures (>373 K), or toxic reducing agents. Here, we report a noble-metal-free heterogeneous catalytic system driven with alcohol as a reducing agent at room temperature. Photoirradiation (λ 2) with alcohol promotes efficient and selective deoxygenation of epoxides into alkenes. This noble-metal-free catalytic deoxygenation is facilitated by the combination of electron transfer from surface Ti3+ atoms on TiO2 to epoxides, which promotes deoxygenation of epoxides, and photocatalytic action of TiO2, which regenerates oxidized surface Ti atoms with alcohol as a reducing agent.
The cascade coupling/iodoaminocyclization reaction of trifluoroacetimidoyl chlorides and allylamines: metal-free access to 2-trifluoromethyl-imidazolines
Chen, Zhengkai,Du, Shiying,Song, Yufei,Wang, Le-Cheng,Wu, Xiao-Feng
supporting information, p. 6115 - 6119 (2021/07/21)
A metal-free cascade coupling/iodoaminocyclization reaction for the rapid assembly of 2-trifluoromethyl-imidazolines has been disclosed. The transformation applies readily accessible trifluoroacetimidoyl chlorides, allylamines andN-iodosuccinimides as the starting substrates, achieving an efficient and straightforward pathway to construct diverse imidazoline derivatives. Excellent efficiency of the reaction is observed (higher than 90% isolated yield for half of the examples), and the obtained imidazoline products bearing a pendent iodomethyl group could be easily transformed into other synthetically valuable compounds.
1,3-Difunctionalization of β-alkyl nitroalkenes via combination of Lewis base catalysis and radical oxidation
Wang, Ye,Zheng, Lei,Shi, Xiaodong,Chen, Yunfeng
supporting information, p. 886 - 889 (2021/02/01)
Upon treatment with a Lewis base catalyst, β-alkyl-substituted nitroalkenes could be readily converted into allylic nitro compounds. Examples of either C-1 or C-3 functionalization methods have been reported through nitro-elimination, giving alkene products. In this work, successful 1,3-difunctionalization was achieved through a synergetic Lewis base catalysis and TBHP radical oxidation, giving vinylic alkoxyamines in good to excellent yields. This work further extended the general synthetic application of β-alkyl nitroalkenes.
