69248-88-0Relevant academic research and scientific papers
Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity
Huang, He,Lambert, Tristan H.,Strater, Zack M.
supporting information, (2020/02/04)
The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-fre
O-H hydrogen bonding promotes H-atom transfer from α C-H bonds for C-alkylation of alcohols
Jeffrey, Jenna L.,Terrett, Jack A.,MacMillant, David W.C.
, p. 1532 - 1536 (2015/10/05)
The efficiency and selectivity of hydrogen atom transfer from organic molecules are often difficult to control in the presence of multiple potential hydrogen atom donors and acceptors. Here, we describe the mechanistic evaluation of a mode of catalytic activation that accomplishes the highly selective photoredox a-alkylation/lactonization of alcohols with methyl acrylate via a hydrogen atom transfer mechanism. Our studies indicate a particular role of tetra-n-butylammonium phosphate in enhancing the selectivity for α C-H bonds in alcohols in the presence of allylic, benzylic, α-C=O, and α-ether C-H bonds.
Generation and Cycloaddition of Oxallyl Intermediates from 2-Bromo-3-pentanone and Pentachloroacetone in 2,2,3,3-Tetrafluoro-1-propanol
Foehlisch, Baldur,Gehrlach, Eberhard,Geywitz, Barbara
, p. 1815 - 1824 (2007/10/02)
2-Bromo-3-pentanone (1) reacts with cyclopentadiene, spirohepta-4,6-diene, furan, 2,5-dimethylfuran, and ω-functionalized 2-alkylfurans in 2,2,3,3-tetrafluoro-1-propanol/sodium 2,2,3,3-tetrafluoropropoxide to form the cycloadducts of the oxallyl intermediate 3 in high yields.The other 1,3-dienes investigated gave low yields of the corresponding cycloadducts.With 4-methyl-1,3-pentadiene and 2-methoxy-1,3-butadiene, cycloadducts are observed.Tetrachloroallylium-2-olate, generated from 1,1,1,3,3-pentachloro-2-propanone (25) undergoes cycloadditions to 26-28 with furan and the substituted furans 22-24 in moderate yields.These cycloadducts were dechlorinated by the Zn/Cu couple.The intramolecular Claisen condensation of the bicyclic oxoester 30 affords the enolized tricyclic 1,3-diketone 34 which can be methylated stereoselectively at the angular position to give 35.
