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Allyl 4-Chlorophenyl Sulfone as a Versatile 1,1-Synthon for Sequential α-Alkylation/Cobalt-Catalyzed Allylic Substitution
| Title: | Allyl 4-Chlorophenyl Sulfone as a Versatile 1,1-Synthon for Sequential α-Alkylation/Cobalt-Catalyzed Allylic Substitution |
| Authors: | Sekino, Tomoyuki Browse this author | | Sato, Shunta Browse this author | | Kuwabara, Kazuki Browse this author | | Takizawa, Koji Browse this author | | Yoshino, Tatsuhiko Browse this author →KAKEN DB | | Kojima, Masahiro Browse this author →KAKEN DB | | Matsunaga, Shigeki Browse this author →KAKEN DB |
| Keywords: | cobalt catalysis | | photoredox catalysis | | metallaphotoredox | | allylation | | sulfones | | regioselectivity |
| Issue Date: | 1-Jul-2020 |
| Publisher: | Georg Thieme Verlag |
| Journal Title: | Synthesis-stuttgart |
| Volume: | 52 |
| Issue: | 13 |
| Start Page: | 1934 |
| End Page: | 1946 |
| Publisher DOI: | 10.1055/s-0040-1707524 |
| Abstract: | Despite 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. |
| Rights: | ©2020 Georg Thieme Verlag Stuttgart · New York |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/82127 |
| Appears in Collections: | 薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 小島 正寛
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