Citation: Liu Lantao, Chen Yingyinga, Zhang An'an, Liu Xue, Zhang Li, Bai Jingru, Li Heng, Mao Guoliang. Palladium Catalyzed Allylic Amination of Cinnamyl Carbonates with Acyl Hydrazones[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 475-481. doi: 10.6023/cjoc201808013 shu

Palladium Catalyzed Allylic Amination of Cinnamyl Carbonates with Acyl Hydrazones

Liu Lantao ^a,, ,
Chen Yingyinga ^a,b ,
Zhang An'an ^a ,
Liu Xue ^a,c ,
Zhang Li ^a ,
Bai Jingru ^a ,
Li Heng ^c ,
Mao Guoliang ^b,,

a.
College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000
b.
College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing 163318
c.
College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Corresponding author: Liu Lantao, liult05@iccas.ac.cn Mao Guoliang, maoguoliang@nepu.edu.cn
Received Date: 13 August 2018
Revised Date: 3 September 2018
Available Online: 10 February 2018
Fund Project: the National Natural Science Foundation of China 21572126the Program for Science & Technology Innovation Talents in Universities of Henan Province 14HASTIT016the Program of Science and Technology Innovation Talents of Henan Province 2018JQ0011Project supported by the National Natural Science Foundation of China (No. 21572126), the Program for Science & Technology Innovation Talents in Universities of Henan Province (No. 14HASTIT016) and the Program of Science and Technology Innovation Talents of Henan Province (No. 2018JQ0011)

Figures(2)

Allylic amines moiety exists extensively in natural products, medicines and functional materials. In addition, they are also a kind of versatile building blocks for organic synthesis. Using CH₃CN as solvent, the palladium catalyzed allyl amination of cinnamyl carbonate and acylhydrazone compounds was realized under argon. The linear product was formed selectively and the up to 99% yield was obtained. The reaction has features of base free, mild reaction condition, simple operation and broad substrate scope.
- paladium catalysis,
- allylic amination,
- cinnamyl carbonate
1. [1]
2. [2]
3. [3]
  (a) Monk, J. P.; Brogden, R. N. Drugs 1991, 42, 659.
  (b) Birnbaum, J. E. J. Am. Acad. Dermatol. 1990, 23, 782.
  (c) Xu, Z.; Wang, D. S.; Yu, X.; Yang Y.; Wang, D. Adv. Synth. Catal. 2017, 359, 3332.
4. [4]
  (a) Stuetz, A.; Petranyi, G. J. Med. Chem. 1984, 27, 1539.
  (b) Rudisill, D. E.; Castonguay, L. A.; Me, J. K. Tetrahedron Lett. 1988, 29, 1509.
  (c) Balfour, J. A.; Fauids, D. Drugs 1992, 43, 259.
  (d) Ge, C.; Sang, X.; Yao, W.; Zhang L.; Wang, D. Green Chem. 2018, 20, 1805.
5. [5]
  (a) Andersson, P. G.; Backvall, J. E. In Handbook of Organopalladium Chemistry for Organic Synthesis, Ed.: Negishi, E., Wiley-Interscience, New York, 2002, p. 1859.
  (b) Davies, H. M. L.; Long, M. S. Angew. Chem., Int. Ed. 2005, 44, 3518.
  (c) Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Wiley-VCH, Weinheim, 2004, Vol. 2, p. 699.
  (d) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis, Ed.: Negishi, E., Wiley-Interscience, New York, 2002, p. 1051.
6. [6]
  (a) Ranerand, K. D.; Ward, A. D. Aust. J. Chem. 1991, 44, 1749.
  (b) Cooper, M. A.; Lucas, M. A.; Taylor, J. M.; Ward, A. D.; Williamson, N. M. Synthesis 2001, 621.
  (c) Vicente, R. Org. Biomol. Chem. 2011, 9, 6469.
7. [7]
  (a) Schultz, D. M.; Wolfe, J. P. Org. Lett. 2010, 12, 1028.
  (b) Caddick, S.; Koe, W. Tetrahedron Lett. 2002, 43, 9347.
  (c) Sharma, V.; Kumar, P.; Pathak, D. J. Heterocycl. Chem. 2010, 47, 491.
  (d) Lu, T.; Lu, Z.; Ma, Z. X.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2013, 113, 4862.
8. [8]
  Cho, C. S.; Kim, J. S.; Oh, B. H. Tetrahedron 2000, 56, 7747. doi: 10.1016/S0040-4020(00)00694-3
9. [9]
  Cui, X. M. Chlor-Alkali Ind. 2000, 5, 172192(in Chinese).
10. [10]
11. [11]
  Lee, O. Y.; Law, K. L.; Yang, D. Org. Lett. 2009, 11, 3302. doi: 10.1021/ol901111g
12. [12]
  (a) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364.
  (b) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941.
  (c) Zhou, C. Y.; Zhu, S. F.; Wang, L. X., Zhou, Q. L. J. Am. Chem. Soc. 2010, 132, 10955.
  (d) Holmes, M.; Schwartz, L. A.; Krische, M. J. Chem. Rev. 2018, 118, 6026.
13. [13]
  (a) Xie, Y. J.; Hu, J. H.; Wang, Y. Y.; Xia, C. G.; Huang, H. J. Am. Chem. Soc. 2012, 134, 20613.
  (b) Liu, Y.; Xie, Y.; Wang, H.; Huang, H. J. Am. Chem. Soc. 2016, 138, 4314.
14. [14]
  (a) Bäckvall, J. E.; Nordberg, R. E.; Nyström, J. E.; Hoegberg, T.; Ulff, B. J. Org. Chem. 1981, 46, 3479.
  (b) You, S. L.; Zhu, X. Z.; Luo, Y. M.; Hou, X. L.; Dai, L. X. J. Am. Chem. Soc. 2001, 123, 7471.
  (c) Nagano, T.; Kobayashi, S. J. Am. Chem. Soc. 2009, 131, 4200.
  (d) Xie, Y. J.; Hu, J. H.; Wang, Y. Y.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2012, 134, 20613.
  (e) Dubovyk, I.; Watson, I. D. G.; Yudin, A. K. J. Org. Chem. 2013, 78, 1559.
  (f) Cai, A. J.; Guo, W. S.; Martínez-Rodríguez, L.; Kleij, A. W. J. Am. Chem. Soc. 2016, 138, 14194.
  (g) Li, Y. G.; Li, L.; Yang, M. Y.; Kantchev, E. A. B. J. Org. Chem. 2017, 82, 4907.
15. [15]
  (a) Trost, B. M.; Zhang, T.; Sieber, J. D. Chem. Sci. 2010, 1, 427.
  (b) Evans, P.; Grange, R.; Clizbe, E. Synthesis 2016, 48, 2911.
  (c) Guo, W.; Cai, A.; Xie, J.; Kleij, A. W. Angew. Chem., Int. Ed. 2017, 56, 11797.
  (d) Xia, C.; Shen, J.; Liu, D.; Zhang, W. Org. Lett. 2017, 19, 4251.
  (e) Wang, Y. N.; Wang, B. C.; Zhang, M. M.; Gao, X. W.; Li, T. R.; Lu, L. Q.; Xiao, W. J. Org. Lett. 2017, 19, 4094.
16. [16]
  Yao, L.; Wang, C. J. Adv. Synth. Catal. 2015, 357, 384. doi: 10.1002/adsc.201400790
17. [17]
  Lu, B.; Feng, B.; Ye, H.; Chen, J. R.; Xiao, W. J. Org. Lett. 2018, 20, 3473. doi: 10.1021/acs.orglett.8b01226
18. [18]
  Ouyang, K.; Xi, Z. Acta Chim. Sinica 2013, 71, 13(in Chinese).
1. [1]
  Jiayi Yang , Jianxiu Hao , Huacong Zhou , Quansheng Liu . “Gorgeous Transformation” of Carbon Dioxide into Cyclic Carbonates: Catalyst Types and Roles. University Chemistry, 2026, 41(2): 178-189. doi: 10.12461/PKU.DXHX202502105
2. [2]
  Yajin Li , Huimin Liu , Lan Ma , Jiaxiong Liu , Dehua He . Photothermal Synthesis of Glycerol Carbonate via Glycerol Carbonylation with CO₂ over Au/Co₃O₄-ZnO Catalyst. Acta Physico-Chimica Sinica, 2024, 40(9): 2308005-0. doi: 10.3866/PKU.WHXB202308005
3. [3]
  Haiqiang Lin , Weizheng Weng , Jingdong Lin , Mingshu Chen , Xueming Fang , Lefu Yang . Diverse Variables-Driven Catalytic Optimization: Experimental Enhancement and Instructional Design for Selective Methane Oxidation on Supported Nickel-based Catalysts. University Chemistry, 2025, 40(11): 327-336. doi: 10.12461/PKU.DXHX202505106
4. [4]
  Chao WU , Qingxiu SHI , Tao XU , Zhengxi PENG , Zhongping XIONG , Yinglin ZHANG , Yujun SI , Chaozhong GUO . Enhancement of oxygen reduction reaction performance of iron-nitrogen doped carbon based catalysts by sodium carboxymethyl cellulose pre-deoxygenation. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 737-746. doi: 10.11862/CJIC.20250305
5. [5]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044
6. [6]
  Dan Li , Hui Xin , Xiaofeng Yi . Comprehensive Experimental Design on Ni-based Catalyst for Biofuel Production. University Chemistry, 2024, 39(8): 204-211. doi: 10.3866/PKU.DXHX202312046
7. [7]
  Huiwei Ding , Bo Peng , Zhihao Wang , Qiaofeng Han . Advances in Metal or Nonmetal Modification of Bismuth-Based Photocatalysts. Acta Physico-Chimica Sinica, 2024, 40(4): 2305048-0. doi: 10.3866/PKU.WHXB202305048
8. [8]
  Yushan Cai , Fang-Xing Xiao . Revisiting MXenes-based Photocatalysis Landscape: Progress, Challenges, and Future Perspectives. Acta Physico-Chimica Sinica, 2024, 40(8): 2306048-0. doi: 10.3866/PKU.WHXB202306048
9. [9]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-0. doi: 10.3866/PKU.WHXB202405016
10. [10]
  Haodong JIN , Qingqing LIU , Chaoyang SHI , Danyang WEI , Jie YU , Xuhui XU , Mingli XU . NiCu/ZnO heterostructure photothermal electrocatalyst for efficient hydrogen evolution reaction. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1068-1082. doi: 10.11862/CJIC.20250048
11. [11]
  Wenruo NI , Hongpeng LI , Yun ZHANG , Yiran TIAN , Jiehui RUI , Yingcheng TONG , Xiaolin PI , Zhenyan TANG . Research progress of ruthenium alloy catalysts in hydrogen evolution reaction. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 23-44. doi: 10.11862/CJIC.20250188
12. [12]
  Xue Liu , Lipeng Wang , Luling Li , Kai Wang , Wenju Liu , Biao Hu , Daofan Cao , Fenghao Jiang , Junguo Li , Ke Liu . Research on Cu-Based and Pt-Based Catalysts for Hydrogen Production through Methanol Steam Reforming. Acta Physico-Chimica Sinica, 2025, 41(5): 100049-0. doi: 10.1016/j.actphy.2025.100049
13. [13]
  Haoyu Sun , Dun Li , Yuanyuan Min , Yingying Wang , Yanyun Ma , Yiqun Zheng , Hongwen Huang . Hierarchical Palladium-Copper-Silver Porous Nanoflowers as Efficient Electrocatalysts for CO₂ Reduction to C₂₊ Products. Acta Physico-Chimica Sinica, 2024, 40(6): 2307007-0. doi: 10.3866/PKU.WHXB202307007
14. [14]
  Hailang JIA , Yujie LU , Pengcheng JI . Preparation and properties of nitrogen and phosphorus co-doped graphene carbon aerogel supported ruthenium electrocatalyst for hydrogen evolution reaction. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2327-2336. doi: 10.11862/CJIC.20250021
15. [15]
  Dong Xiang , Kunzhen Li , Kanghua Miao , Ran Long , Yujie Xiong , Xiongwu Kang . Amine-Functionalized Copper Catalysts: Hydrogen Bonding Mediated Electrochemical CO₂ Reduction to C₂ Products and Superior Rechargeable Zn-CO₂ Battery Performance. Acta Physico-Chimica Sinica, 2024, 40(8): 2308027-0. doi: 10.3866/PKU.WHXB202308027
16. [16]
  Wen YANG , Didi WANG , Ziyi HUANG , Yaping ZHOU , Yanyan FENG . La promoted hydrotalcite derived Ni-based catalysts: In situ preparation and CO₂ methanation performance. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 561-570. doi: 10.11862/CJIC.20230276
17. [17]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-Based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-0. doi: 10.3866/PKU.WHXB202406029
18. [18]
  Xiyuan Zhang , Rui Dong , Yang Yang , Jiapeng Ding , Zhiwei Miao . Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(9): 361-367. doi: 10.12461/PKU.DXHX202410062
19. [19]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . Effect of Interlayer Anions in Layered Double Hydroxides on the Photothermocatalytic CO₂ Methanation of Derived Ni-Al₂O₃ Catalysts. Acta Physico-Chimica Sinica, 2025, 41(1): 100002-0. doi: 10.3866/PKU.WHXB202309002
20. [20]
  Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(1343)
HTML views(136)

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