4.8 Article

Cobalt-Catalyzed, Aminoquinoline-Directed Functionalization of Phosphinic Amide sp2 C-H Bonds

Journal

ACS CATALYSIS
Volume 6, Issue 2, Pages 551-554

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.5b02391

Keywords

cobalt; C-H functionalization; phosphinic amides; alkenes; alkynes

Funding

  1. Welch Foundation [E-0044]
  2. NIGMS [R01GM077635]
  3. University of Houston

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In this paper, we introduce arylphosphinic acid aminoquinoline amides as competent substrates for cobalt-catalyzed sp(2) C-H bond functionalization. Specifically, the feasibility of their coupling with alkynes, alkenes, and allyl pivalate has been demonstrated. Reactions are catalyzed by simple Co(NO3)(2) hydrate in ethanol or mixed dioxane/tBuOH solvent in the presence of Mn(OAc)(3)center dot 2H(2)O additive, sodium pivalate, or acetate base and use oxygen from the air as an oxidant. Directing group removal affords ortho-functionalized P,P-diarylphosphinic acids.

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