2024-03-29T13:48:08Zhttps://eprints.lib.hokudai.ac.jp/dspace-oai/requestoai:eprints.lib.hokudai.ac.jp:2115/821272022-11-17T02:08:08Zhdl_2115_20044hdl_2115_124Allyl 4-Chlorophenyl Sulfone as a Versatile 1,1-Synthon for Sequential α-Alkylation/Cobalt-Catalyzed Allylic SubstitutionSekino, TomoyukiSato, ShuntaKuwabara, KazukiTakizawa, KojiYoshino, TatsuhikoKojima, MasahiroMatsunaga, Shigekicobalt catalysisphotoredox catalysismetallaphotoredoxallylationsulfonesregioselectivity460Despite their unique potential as rare 1,1-dipole synthons, allyl sulfones are rarely used in target-oriented syntheses, likely due to the lack of a general catalytic method for their branch-selective allylic substitution. Herein, we identified allyl 4-chlorophenyl sulfone as a versatile linchpin for both base-mediated alpha-derivatization and subsequent cobalt-catalyzed allylic substitution. The sequential transformations allow for highly regioselective access to branched allylic substitution products with a variety of aliphatic side chains. The photoredox-enabled- -cobalt catalysis is indispensable for achieving high yields and regioselectivity- for the desulfonylative substitution in contrast to traditional metal-catalyzed protocols, which lead to inferior outcomes in the corresponding transformations.Georg Thieme VerlagJournal Articleapplication/pdfhttp://hdl.handle.net/2115/82127https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/82127/1/WoS_94840_Kojima.pdf0039-7881Synthesis-stuttgart5213193419462020-07-01enginfo:doi/10.1055/s-0040-1707524©2020 Georg Thieme Verlag Stuttgart · New Yorkauthor