Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (3): 830-835.DOI: 10.6023/cjoc201812051 Previous Articles     Next Articles

Special Issue: 碳氢活化合辑2018-2019 元素有机化学合辑2018-2019

Notes

钯催化下稳定磷叶立德与烯丙基醇的脱水偶联反应

马献涛a, 于静a, 马瑞甜a, 燕然a, 张振雷a,b   

  1. a 信阳师范学院化学化工学院 信阳 464000;
    b 阜阳师范学院化学与材料工程学院 阜阳 236037
  • 收稿日期:2018-12-31 修回日期:2019-01-27 出版日期:2019-03-25 发布日期:2019-02-22
  • 通讯作者: 马献涛, 张振雷 E-mail:xiantaoma@126.com;helenken@mail.ustc.edu.cn
  • 基金资助:

    河南省高等学校重点科研项目(No.19B150018)、信阳师范学院“南湖学者奖励计划”青年项目和信阳师范学院青年骨干教师资助计划(No.2018GGJS-05)资助项目.

Palladium-Catalyzed Dehydrative Cross Couplings of Stabilized Phosphorus Ylides with Allylic Alcohols

Ma Xiantaoa, Yu Jinga, Ma Ruitiana, Yan Rana, Zhang Zhenleia,b   

  1. a College of Chemistry and Chemical Engineering, Xinyang Normal University, Xinyang 464000;
    b School of Chemistry and Material Engineering, Fuyang Normal University, Fuyang 236037
  • Received:2018-12-31 Revised:2019-01-27 Online:2019-03-25 Published:2019-02-22
  • Contact: 10.6023/cjoc201812051 E-mail:xiantaoma@126.com;helenken@mail.ustc.edu.cn
  • Supported by:

    Project supported by the Scientific Research Project of Henan Province (No. 19B150018), the Nanhu Scholars Program for Young Scholars of Xinyang Normal University and the Young Core Instructor Program of Xinyang Normal University (No. 2018GGJS-05).

A dehydrative cross coupling of ketone-stabilized phosphorus ylides with the readily available allylic alcohols followed by an one-pot Wittig reaction is developed. A range of functional 1,4-dienes could be obtained in 52%~95% isolated yields in the presence of 5 mol% Pd(PPh3) 4 and 20 mol% B(OH) 3. The same method can be extended to ester or nitrile-stabi-lized phosphorus ylides, affording the corresponding 1,4-dienes in moderate yields.

Key words: stabilized phosphorus ylides, allylic alcohols, dehydrative cross couplings, palladium catalysis