13616-47-2Relevant academic research and scientific papers
Oxidative Kinetic Resolution of Cyclic Benzylic Ethers
Liu, Lei,Liu, Ziqiang,Ma, Yingang,Sun, Shutao
, p. 176 - 180 (2020/10/30)
A manganese-catalyzed oxidative kinetic resolution of cyclic benzylic ethers through asymmetric C(sp3)?H oxidation is reported. The practical approach is applicable to a wide range of 1,3-dihydroisobenzofurans bearing diverse functional groups and substituent patterns at the α position with extremely efficient enantiodiscrimination. The generality of the strategy was further demonstrated by efficient oxidative kinetic resolution of another type of five-membered cyclic benzylic ether, 2,3-dihydrobenzofurans, and six-membered 6H-benzo[c]chromenes. Direct late-stage oxidative kinetic resolution of bioactive molecules that are otherwise difficult to access was further explored.
Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis
Rivero, Alexandra R.,Fodran, Peter,Ondrejková, Alica,Wallentin, Carl-Johan
, p. 8436 - 8440 (2020/11/03)
A mechanistically divergent method is described that, employing a commercially available hypervalent iodine(III) reagent, generates alkoxy radicals from 1°, 2°, and 3° alcohols and allows their use in the functionalization of C(sp3)-H and C(sp2)-H bonds. This visible-light photoredox catalysis produces alkyl ethers via 1,5/6-hydrogen atom transfer or aryl ethers via 1,5-addition. This mild methodology provides a practical strategy for the synthesis of acetals, orthoesters, tetrahydrofurans, and chromanes.
