Palladium(II)-Catalyzed Aerobic 1,2-Diacetoxylation of Conjugated Dienes

  • Ju Chenyang ,
  • Wu Zhengxing ,
  • Li Yunyi ,
  • Zhang Wanbin
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  • Shanghai Key Laboratory for Molecular Engineering and Chiral Drugs, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiaotong University, Shanghai, 200240

Received date: 2020-04-16

  Revised date: 2020-05-19

  Online published: 2020-05-29

Supported by

Project supported by the Shanghai Municipal Education Commission (No. 201701070002E00030), the Shanghai Sailing Program (No. 19YF1421900), the Science and Technology Commission of Shanghai Municipality (No. 19JC1430100), and the National Natural Science Foundation of China (Nos. 21620102003, 21831005, 21901158, 21991112).

Abstract

1,2-Diols have important applications in pesticides, chiral medicines and fine chemicals. A Pd(II)-catalyzed 1,2-diacetoxylation method using readily available acetic acid as the oxygen source and oxygen as the oxidant was developed. For the 1,2-diacetoxylation of conjugated dienes, the reaction proceeds with high 1,2-regioselectivity. This protocol has good substrate scope for conjugated dienes possessing aryl-, ester-and carbonyl groups. The catalytic products can be transformed to 1,2-diols through simple alcoholysis or hydrolysis, therefore it is an efficient method for the synthesis of 1,2-diols.

Cite this article

Ju Chenyang , Wu Zhengxing , Li Yunyi , Zhang Wanbin . Palladium(II)-Catalyzed Aerobic 1,2-Diacetoxylation of Conjugated Dienes[J]. Chinese Journal of Organic Chemistry, 2020 , 40(11) : 3925 -3933 . DOI: 10.6023/cjoc202004025

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