Electron transfer-induced reduction of organic halides with amines Takahide Fukuyama, Yuki Fujita, Hayato Miyoshi, Ilhyong Ryu, Shih-Chieh Kao, Yen-Ku Wu Chem. Commun., 2018, , pp. - DOI: 10.1039/C8CC02445F
Reduction of a variety of organo halides was examined by using amines as a sacrificial hydrogen source. UV light-induced reduction of vinyl and aryl halides with triethylamine proceeded smoothly to give the corresponding reduced products. High temperature heating also caused the reduction and DABCO (1,4-diazabicyclo[2.2.2]octane) also served as a good reducing reagent.
Palladium/Light Induced Radical Alkenylation and Allylation of Alkyl Iodides Using Alkenyl and Allylic Sulfones Shuhei Sumino, Misae Uno, Hsin-Ju Huang, Yen-Ku Wu, Ilhyong Ryu Org. Lett., 2018, 20, 4 pp. 1078 - 1081 DOI: 10.1021/acs.orglett.7b04050
Alkenylation and allylation of alkyl iodides with alkenyl and allyl sulfones, respectively, took place under Pd/photoirradiation system. The initial alkyl radical, derived from a single electron transfer between Pd(0) and RI, underwent the title transformations. Pd(0) was regenerated through a reductive elimination of PhSO2PdI, which is formed by the combination of the sulfonyl radical and the palladium radical. The addition of water was effective, presumably by pushing the equilibrium through hydrolysis of PhSO2I.
Site-Selective C–H Functionalization by Decatungstate Anion Photocatalysis: Synergistic Control by Polar and Steric Effects Expands the Reaction Scope Davide Ravelli, Maurizio Fagnoni, Takahide Fukuyama, Tomohiro Nishikawa, Ilhyong Ryu ACS Catal., 2018, 8, 1 pp. 701 - 713 DOI: 10.1021/acscatal.7b03354
The synergistic control of the SH2 transition states of hydrogen abstraction by polar and steric effects provides a promising strategy in achieving site-selective C(sp3)–H functionalization under decatungstate anion photocatalysis. By using this photocatalytic approach, the C–H bonds of alkanes, alcohols, ethers, ketones, amides, esters, nitriles, and pyridylalkanes were functionalized site-selectively. In the remarkable case of a 2,4-disubstituted cyclohexanone bearing five methyl, five methylene, and three methine C–H bonds, one methine C–H bond in the isoamyl tether was selectively functionalized.