Allyl 4-Chlorophenyl Sulfone as a Versatile 1,1-Synthon for Sequential α-Alkylation/Cobalt-Catalyzed Allylic Substitution

Sekino, Tomoyuki; Sato, Shunta; Kuwabara, Kazuki et al.

Synthesis-stuttgart, 2020, 52(13), 1934-1946

Permalink : https://hdl.handle.net/2115/82127

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アクセス権
open access
URI
https://hdl.handle.net/2115/82127
タイトル
Allyl 4-Chlorophenyl Sulfone as a Versatile 1,1-Synthon for Sequential α-Alkylation/Cobalt-Catalyzed Allylic Substitution
著者
Sekino, Tomoyuki ; Sato, Shunta ; Kuwabara, Kazuki ; Takizawa, Koji ; Yoshino, Tatsuhiko ; Kojima, Masahiro ; Matsunaga, Shigeki
著者名
Sekino, Tomoyuki
著者名
Sato, Shunta
著者名
Kuwabara, Kazuki
著者名
Takizawa, Koji
e-Rad_Researcher
50756179
著者名
Yoshino, Tatsuhiko
e-Rad_Researcher
90824714
著者名
Kojima, Masahiro
e-Rad_Researcher
50334339
著者名
Matsunaga, Shigeki
言語
英語
キーワード
cobalt catalysis
photoredox catalysis
metallaphotoredox
allylation
sulfones
regioselectivity
発行日
2020-07-01
出版者
Georg Thieme Verlag
収録物名
Synthesis-stuttgart
巻(号)
52(13)
ページ
1934-1946
抄録
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.
資源タイプ
学術雑誌論文
出版タイプ
Accepted Manuscript
権利情報
©2020 Georg Thieme Verlag Stuttgart · New York
PISSN
0039-7881
関連情報 (isVersionOf)
出版社版DOI
https://doi.org/10.1055/s-0040-1707524