4.7 Article

Hf(OTf)4-Catalyzed 1,6-Conjugate Addition of 2-Alkyl-azaarenes to para-Quinone Methides

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 4, Pages 3615-3624

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02982

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Funding

  1. National Natural Science Foundation of China [21702013]
  2. Fundamental Research Funds for the Central Universities [XK1802-6]

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A carbon-carbon bond formation reaction catalyzed by Hf(OTf)(4) between 2-alkyl-azaarenes and para-quinone methides (p-QMs) was reported, providing rapid access to a variety of triarylethane products in good yields. The catalyst loading could be reduced to 1 mol%. Studies on scale-up reactions and product derivatization were also presented.
Herein we reported a Hf(OTf)(4)-catalyzed carbon-carbon bond formation reaction between 2-alkyl-azaarenes and para-quinone methides (p-QMs). This 1,6-conjugate addition protocol offered rapid access to a large array of triarylethane products in good yields. The catalyst loading could be reduced to 1 mol %. Studies pertinent to scale-up reaction and product derivatization were also presented.

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