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

• Sekino, Tomoyuki

• Sato, Shunta

• Kuwabara, Kazuki

• Takizawa, Koji

• Yoshino, Tatsuhiko

• Kojima, Masahiro

• Matsunaga, Shigeki

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.

収録刊行物

• Synthesis-stuttgart

  Synthesis-stuttgart 52 (13), 1934-1946, 2020-07-01

  Georg Thieme Verlag

キーワード

• cobalt catalysis
• photoredox catalysis
• metallaphotoredox
• allylation
• sulfones
• regioselectivity

詳細情報

• CRID: 1050288603070200320
• NII論文ID: 120007097396
• DOI: 10.1055/s-0040-1707524
• ISSN: 1437210X
• ISSN: 00397881
• HANDLE: 2115/82127
• Web Site: http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0040-1707524.pdf
• 本文言語コード: en
• 資料種別: journal article
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