Citation: 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 shu

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

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

Corresponding author: Wu Zhengxing, wzxtheway@sjtu.edu.cn Zhang Wanbin, wanbin@sjtu.edu.cn
Received Date: 16 April 2020
Revised Date: 19 May 2020
Available Online: 27 May 2020
Fund Project: the Shanghai Sailing Program 19YF1421900the National Natural Science Foundation of China 21991112the National Natural Science Foundation of China 21901158the Shanghai Municipal Education Commission 201701070002E00030the National Natural Science Foundation of China 21831005the Science and Technology Commission of Shanghai Municipality 19JC1430100the National Natural Science Foundation of China 21620102003Project 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)

Figures(4)

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.
- palladium,
- conjugated diene,
- 1, 2-diacetoxylation,
- 1, 2-diol
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