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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 8: 3192 - 3203

DOI: https://doi.org/10.6023/cjoc202104003

ARTICLES

NaOtBu-Catalyzed Hydrophosphonylation of δ-CN-δ-aryl-disubstituted para-Quinone Methides with Phosphine Oxides

  • Donglin Wang ,
  • Linglong Kan ,
  • Yudao Ma ,
  • Lei Liu
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  • a School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100
    b Shenzhen Research Institute of Shandong University, Shenzhen, Guangdong 518057
*Corresponding authors.E-mail: ;
E-mail:

Received date: 2021-04-01

  Revised date: 2021-04-29

  Online published: 2021-05-14

Supported by

National Natural Science Foundation of China(21971148); Shenzhen Special Funds(JCYJ20190807093805572)

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Abstract

An effective method for the construction of diarylmethyl phosphorus oxides containing CN-substituted quaternary stereocenters via 1,6-conjugated addition has been developed. Under mild condition, the hydrophosphonylation process of δ-CN-δ-aryl-disubstituted para-quinone methides (p-QMs) with diarylphosphine oxides underwent smoothly, affording the desired products in 74%~92% yields. In addition, this protocol features great functional group tolerance and displays a broad substrate scope. Diaryl (multi-substituted methyl) phosphorus oxides bearing CN-substituted quaternary stereocenters synthesized by this efficient method has the potential application in the discovery of new ligands.

Key words： para-quinone methide; diarylmethyl phosphorus oxide; hydrophosphonylation; quaternary stereocenter; 1,6- conjugate addition

Cite this article

Donglin Wang , Linglong Kan , Yudao Ma , Lei Liu . NaOtBu-Catalyzed Hydrophosphonylation of δ-CN-δ-aryl-disubstituted para-Quinone Methides with Phosphine Oxides[J]. Chinese Journal of Organic Chemistry, 2021 , 41(8) : 3192 -3203 . DOI: 10.6023/cjoc202104003

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