Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3192-3203.DOI: 10.6023/cjoc202104003 Previous Articles     Next Articles

ARTICLES

叔丁醇钠催化的δ-腈基-δ-芳基-双取代的对亚甲基苯醌和二芳基氧磷的磷氢化反应研究

王东琳a, 阚玲珑a, 马玉道a,*(), 刘磊a,b,*()   

  1. a 山东大学化学与化工学院 济南 250100
    b 山东大学深圳研究院 广东深圳 518057
  • 收稿日期:2021-04-01 修回日期:2021-04-29 发布日期:2021-05-14
  • 通讯作者: 马玉道, 刘磊
  • 基金资助:
    国家自然科学基金(21971148); 深圳面上资助项目(JCYJ20190807093805572)

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

Donglin Wanga, Linglong Kana, Yudao Maa(), Lei Liua,b()   

  1. a School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100
    b Shenzhen Research Institute of Shandong University, Shenzhen, Guangdong 518057
  • Received:2021-04-01 Revised:2021-04-29 Published:2021-05-14
  • Contact: Yudao Ma, Lei Liu
  • Supported by:
    National Natural Science Foundation of China(21971148); Shenzhen Special Funds(JCYJ20190807093805572)

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