4.8 Article

Co-Catalyzed Direct Addition of Allylic C(sp3)-H Bonds to Ketones

Journal

ORGANIC LETTERS
Volume 19, Issue 21, Pages 5876-5879

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02871

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Funding

  1. JSPS [26410108, 26293001, 14J08052]
  2. JST ACT-C [JPMJCR12YM]
  3. Grants-in-Aid for Scientific Research [26293001, 26410108, 14J08052] Funding Source: KAKEN

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By using Co(acac)(2)/Xantphos with AlMe3, the C(sp(3))-H bonds of allylarene derivatives were cleaved for reaction with various ketones, affording the homoallylic alcohols in moderate to good yields. The branch/linear selectivity depended on the steric and electronic factors of the ketone electrophiles. The intermediate in this reaction is thought to be a low-valent allylcobalt(I) species, which exhibits high nucleophilicity toward ketones.

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