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
1. [1]
2. [2]
  (a) Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Chem. Rev. 2005, 105, 2329.
  (b) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890.
  (c) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
  (d) Shi, Z.; Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3381.
  (e) Wu, W.; Jiang, H. Acc. Chem. Res. 2012, 45, 1736.
  (f) Campbell, A. N.; Stahl, S. S. Acc. Chem. Res. 2012, 45, 851.
  (g) Mann, S. E.; Benhamou, L.; Sheppard, T. D. Synthesis 2015, 47, 3079.
  (h) Kočovský, P.; Bäckvall, J.-E. Chem.-Eur. J. 2015, 21, 36.
  (i) Yang, Y.; Lan, J.; You, J. Chem. Rev. 2017, 117, 8787.
  (j) Wang, D.; Weinstein, A. B.; White, P. B.; Stahl, S. S. Chem. Rev. 2018, 118, 2636.
  (k) Tang, X.; Wu, W.; Zeng, W.; Jiang, H. Acc. Chem. Res. 2018, 51, 1092.
3. [3]
  (a) Ely, R. J.; Morken, J. P. Org. Lett. 2010, 12, 4348.
  (b) Burks, H. E.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 9134.
  (c) Bäckvall, J.-E. In Metal Catalyzed Cross-Coupling Reactions, 2nd ed.; Eds.: De Meijere, A.; Diederich, F., Wiley-VCH, Weinheim, 2004, p. 479.
  (d) Bäckvall, J.-E.; Andersson, P. G. J. Am. Chem. Soc. 1992, 114, 6374.
  (e) Aranyos, A.; Szabó, K. J.; Bäckvall, J.-E. J. Org. Chem. 1998, 63, 2523.
  (f) Itami, K.; Palmgren, A.; Thorarensen, A.; Bäckvall, J.-E. J. Org. Chem. 1998, 63, 6466.
  (g) Verboom, R. C.; Persson, B. A.; Bäckvall, J.-E. J. Org. Chem. 2004, 69, 3102.
  (h) Zhang, Z.; Mamba, T.; Yamamoto, E.; Murayama, H.; Ishida, T.; Honma, T.; Fujitani, T.; Tokunaga, M. Appl. Catal. B-Environ. 2019, 246, 100.
4. [4]
  (a) Sinha, S. C.; Keinan, E. J. Org. Chem. 1997, 62, 377.
  (b) Zhang, Y.; Chu, G.; Cui, X.; Han, Z.; Dou, D.; Chen, Y.; Yu, X.; Li, C. Synlett 2010, 1118.
5. [5]
  (a) Kliman, L. T.; Mlynarski, S. N.; Ferris, G. E.; Morken, J. P. Angew. Chem., Int. Ed. 2012, 51, 521.
  (b) Toribatake, K.; Nishiyama, H. Angew. Chem., Int. Ed. 2013, 52, 11011.
  (c) Ishiyama, T.; Yamamoto, M.; Miyaura, N. Chem. Commun. 1997, 689.
6. [6]
  Qian, B.; Xiong, H.; Zhu, N.; Ye, C.; Jian, W.; Bao, H. Tetrahedron Lett. 2006, 57, 3400.
7. [7]
  (a) Huang, J.; Ouyang, L.; Li, J.; Zheng, J.; Yan, W.; Wu, W.; Jiang, H. Org. Lett. 2018, 20, 5090.
  (b) Zhang, Z.; Mamba, T.; Huang, Q.-A.; Murayama, H.; Yamamoto, E.; Honma, T.; Tokunaga, M. Mol. Catal. 2019, 475, 110502.
8. [8]
9. [9]
10. [10]
11. [11]
  Steinhoff, B. A.; King, A. E.; Stahl, S. S. J. Org. Chem. 2006, 71, 1861. doi: 10.1021/jo052192s
12. [12]
  (a) Lin, R.; Yu, Y.; Zhang, Y. Synth. Commun. 1993, 23, 271.
  (b) Lishchynskyi, A.; Muniz, K. Chem.-Eur. J. 2012, 18, 2212.
  (c) Zhang, M.; Watanabe, K.; Tsukamoto, M.; Shibuya, R.; Morimoto, H.; Ohshima, T. Chem.-Eur. J. 2015, 21, 3937.
  (d) Yu, E. C.; Johnson, B. M.; Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2016, 55, 13210.
  (e) Bhowmik, A.; Fernandes, R. A. Org. Lett. 2019, 21, 9203.
13. [13]
  Moro, A. V.; Cardoso, F. S.; Correia, C. R. Org. Lett. 2009, 11, 3642. doi: 10.1021/ol901416e
14. [14]
  Thangavelu, S.; Rajendran, S.; Mukesh, D.; Anju, C. Tetrahedron:Asymmetry 2012, 23, 1360. doi: 10.1016/j.tetasy.2012.09.014
15. [15]
  Ono, M.; Kato, K.; Akita, H. Chem. Pharm. Bull. 2013, 61, 464. doi: 10.1248/cpb.c12-01026
1. [1]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
2. [2]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
3. [3]
  Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
4. [4]
  Xinhao Yan , Guoliang Hu , Ruixi Chen , Hongyu Liu , Qizhi Yao , Jiao Li , Lingling Li . Polyethylene Glycol-Ammonium Sulfate-Nitroso R Salt System for the Separation of Cobalt (II). University Chemistry, 2024, 39(6): 287-294. doi: 10.3866/PKU.DXHX202310073
5. [5]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
6. [6]
  Weihan Zhang , Menglu Wang , Ankang Jia , Wei Deng , Shuxing Bai . 表面硫物种对钯-硫纳米片加氢性能的影响. Acta Physico-Chimica Sinica, 2024, 40(11): 2309043-. doi: 10.3866/PKU.WHXB202309043
7. [7]
  Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
8. [8]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
9. [9]
  Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn²⁺ doped quasi-two-dimensional perovskites (PEA)₂Pb_yMn_1-yBr₄. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
10. [10]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
11. [11]
  Jianding LI , Junyang FENG , Huimin REN , Gang LI . Proton conductive properties of a Hf(Ⅳ)-based metal-organic framework built by 2,5-dibromophenyl-4,6-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1094-1100. doi: 10.11862/CJIC.20240464
12. [12]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
13. [13]
  Cuicui Yang , Bo Shang , Xiaohua Chen , Weiquan Tian . Understanding the Wave-Particle Duality and Quantization of Confined Particles Starting from Classic Mechanics. University Chemistry, 2025, 40(3): 408-414. doi: 10.12461/PKU.DXHX202407066
14. [14]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
15. [15]
  Baohua LÜ , Yuzhen LI . Anisotropic photoresponse of two-dimensional layered α-In₂Se₃(2H) ferroelectric materials. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1911-1918. doi: 10.11862/CJIC.20240105
16. [16]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
17. [17]
  Runhua Chen , Qiong Wu , Jingchen Luo , Xiaolong Zu , Shan Zhu , Yongfu Sun . 缺陷态二维超薄材料用于光/电催化CO₂还原的基础与展望. Acta Physico-Chimica Sinica, 2025, 41(3): 2308052-. doi: 10.3866/PKU.WHXB202308052
18. [18]
  Shiyang He , Dandan Chu , Zhixin Pang , Yuhang Du , Jiayi Wang , Yuhong Chen , Yumeng Su , Jianhua Qin , Xiangrong Pan , Zhan Zhou , Jingguo Li , Lufang Ma , Chaoliang Tan . 铂单原子功能化的二维Al-TCPP金属-有机框架纳米片用于增强光动力抗菌治疗. Acta Physico-Chimica Sinica, 2025, 41(5): 100046-. doi: 10.1016/j.actphy.2025.100046
19. [19]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
20. [20]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362

Get Citation

PDF

XML

Metrics

PDF Downloads(22)
Abstract views(3187)
HTML views(344)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142