Citation: Wu Zhengxing, Zhang Wanbin. Recent Advances in Metal-Catalyzed 1, 2-Difunctionalization of Conjugated Dienes[J]. Chinese Journal of Organic Chemistry, ;2017, 37(9): 2250-2262. doi: 10.6023/cjoc201704031 shu

Recent Advances in Metal-Catalyzed 1, 2-Difunctionalization of Conjugated Dienes

Wu Zhengxing ,
Zhang Wanbin ^,

School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Corresponding author: Zhang Wanbin, wanbin@sjtu.edu.cn
Received Date: 18 April 2017
Revised Date: 22 May 2017
Available Online: 24 September 2017
Fund Project: the Program of Shanghai Subject Chief Scientists 14XD1402300the National Natural Science Foundation of China 21232004the National Natural Science Foundation of China 21672142the Basic Research Foundation of Shanghai Science and Technology Committee 15JC1402200Project supported by the National Natural Science Foundation of China (Nos. 21232004, 21672142), the Program of Shanghai Subject Chief Scientists (No.14XD1402300) and the Basic Research Foundation of Shanghai Science and Technology Committee (No. 15JC1402200)

Figures(9)

The 1, 2-difunctionalization of conjugated dienes is an important homogeneous catalytic reaction. The obtained products through 1, 2-difunctionalization are widely existed in natural products and bioactive compounds, and are also sources of important organic intermediates, in addition, the preserved double bond in the difunctionalized product can be further transformed to give the desired structures or be functionalized sequentially to achieve multi-functionalization. The main difficulties focus on the encountered complex selectivities, including the regioselectivity, chemoselectivity and stereoselectivity in reactions. In recent years, with the development of organometallic chemistry, metal palladium, copper, iron or silver catalyzed 1, 2-difunctionalizations of conjugated dienes have been reported in succession. In some cases the enantioselective 1, 2-difunctionalizations of conjugated dienes were achieved via the introduction of chiral ligands. This review mainly focus on the recent metal catalyzed 1, 2-difunctionalizations of conjugated dienes.
- metal-catalyzed,
- conjugated diene,
- 1, 2-difunctionalization
1. [1]
2. [2]
3. [3]
  Prileschajew, N. Eur. J. Inorg. Chem. 1909, 42, 4811.
4. [4]
  Gilman, H. Organic Chemistry:An Advanced Treatise, Vol. 1, Wiley, New York, 1938, p. 36.
5. [5]
  (a) Criegee, R. Justus Liebigs Ann. Chem. 1936, 522, 75.
  (b) Criegee, R. Angew. Chem. 1937, 50, 153.
6. [6]
  Kwart, H.; Kahn, A. A. J. Am. Chem. Soc. 1967, 89, 1950. doi: 10.1021/ja00984a034
7. [7]
  (a) Sharpless, K. B.; Patrick, D. W.; Truesdale, L. K.; Biller, S. A. J. Am. Chem. Soc. 1975, 97, 2305.
  (b) Chong, A. O.; Oshima, K.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 3420.
8. [8]
  (a) Bäckvall, J.-E. Tetrahedron Lett. 1978, 19, 163.
  (b) Bäckvall, J.-E.; Björkman, E. E. J. Org. Chem. 1980, 45, 2893.
9. [9]
  (a) Sharpless, K. B.; Chong, A. O.; Oshima, K. J. Org. Chem. 1976, 41, 177.
  (b) Hentges, S. G.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 4263.
  (c) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
  (d) Jacobsen, E. N.; Marko, I.; Mungall, W. S.; Schroeder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968.
10. [10]
  (a) Aranyos, A.; Szabó, K. J.; Bäckvall, J.-E. J. Org. Chem. 1998, 63, 2523.
  (b) Itami, K.; Palmgren, A.; Thorarensen, A.; Bäckvall, J.-E. J. Org. Chem. 1998, 63, 6466.
  (c) Palmgren, A.; Larsson, A. L. E.; Bäckvall, J.-E. J. Org. Chem. 1999, 64, 836.
  (d) Löfstedt, J.; Närhi, K.; Dorange, I.; Bäckvall, J.-E. J. Org. Chem. 2003, 68, 7243.
  (e) Verboom, R. C.; Persson, B. A.; Bäckvall, J.-E. J. Org. Chem. 2004, 69, 3102.
  (f) Piera, J.; Persson, A.; Caldentey, X.; Bäckvall, J.-E. J. Am. Chem. Soc. 2007, 129, 14120.
  (g) Burks, H. E.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 9134.
  (h) Schuster, C. H.; Li, B.; Morken, J. P. Angew. Chem. Int. Ed. 2011, 50, 7906.
11. [11]
  Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7571. doi: 10.1021/ja00045a044
12. [12]
  O'Connor, J. M.; Stallman, B. J.; Clark, W. G.; Shu, A. Y. L.; Spada, R. E.; Stevenson, T. M.; Dieck, H. A. J. Org. Chem. 1983, 48, 807. doi: 10.1021/jo00154a010
13. [13]
  (a) Larock, R. C.; Fried, C. A. J. Am. Chem. Soc. 1990, 112, 5882.
  (b) Larock, R. C.; Berrios-Pena, N. G.; Narayanan, K. J. Org. Chem. 1990, 55, 3447.
14. [14]
  (a) Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 762.
  (b) Zhao, B.; Du, H.; Cui, S.; Shi, Y. J. Am. Chem. Soc. 2010, 132, 3523.
15. [15]
  Liao, L.; Jana, R.; Urkalan, K. B.; Sigman, M. S. J. Am. Chem. Soc. 2011, 133, 5784. doi: 10.1021/ja201358b
16. [16]
  Larock, R. C.; Harrison, L. W.; Hsu, M. H. J. Org. Chem. 1984, 49, 3662. doi: 10.1021/jo00193a047
17. [17]
  Bar, G. L. J.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2005, 127, 7308. doi: 10.1021/ja051181d
18. [18]
  Houlden, C. E.; Bailey, C. D.; Ford, J. G.; Gagné, M. R.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2008, 130, 10066. doi: 10.1021/ja803397y
19. [19]
  Xing, D.; Yang, D. Org. Lett. 2013, 15, 4370. doi: 10.1021/ol401901h
20. [20]
  Cooper, S. P.; Booker-Milburn, K. I. Angew. Chem. Int. Ed. 2015, 54, 6496. doi: 10.1002/anie.201501037
21. [21]
  (a) Kagechika, K.; Shibasaki, M. J. Org. Chem. 1991, 56, 4093.
  (b) Kagechika, K.; Ohshima, T.; Shibasaki, M. Tetrahedron 1993, 49, 1773.
  (c) Ohshima, T.; Kagechika, K.; Adachi, A.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1996, 118, 7108.
22. [22]
  Du, H.; Yuan, W.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 11688. doi: 10.1021/ja074698t
23. [23]
  Cornwall, R. G.; Zhao, B.; Shi, Y. Org. Lett. 2013, 15, 796. doi: 10.1021/ol303469a
24. [24]
  Stokes, B. J.; Liao, L.; de Andrade, A. M.; Wang, Q.; Sigman, M. S. Org. Lett. 2014, 16, 4666. doi: 10.1021/ol502279u
25. [25]
  Wu, X.; Lin, H.-C.; Li, M.-L.; Li, L. L.; Han, Z.-Y.; Gong, L.-Z. J. Am. Chem. Soc. 2015, 137, 13476. doi: 10.1021/jacs.5b08734
26. [26]
  Liu, Y.; Xie, Y.; Wang, H.; Huang, H. J. Am. Chem. Soc. 2016, 138, 4314. doi: 10.1021/jacs.6b00976
27. [27]
  Chen, S.-S.; Meng, J.; Li, Y.-H.; Han, Z.-Y. J. Org. Chem., 2016, 81, 9402. doi: 10.1021/acs.joc.6b01611
28. [28]
  Chen, S.-S.; Wu, M.-S.; Han, Z.-Y. Angew. Chem., Int. Ed. 2017, 56, 6641. doi: 10.1002/anie.201702745
29. [29]
  Yuan, W.; Du, H.; Zhao, B.; Shi, Y. Org. Lett. 2007, 9, 2589. doi: 10.1021/ol071105a
30. [30]
  Zhao, B.; Peng, X.; Cui, S.; Shi, Y. J. Am. Chem. Soc. 2010, 132, 11009. doi: 10.1021/ja103838d
31. [31]
  Zhao, B.; Peng, X.; Zhu, Y.; Ramirez, T. A.; Cornwall, R. G.; Shi, Y. J. Am. Chem. Soc. 2011, 133, 20890. doi: 10.1021/ja207691a
32. [32]
  Michaelis, D. J.; Ischay, M. A.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 6610. doi: 10.1021/ja800495r
33. [33]
  Du, H.; Zhao, B.; Yuan, W.; Shi, Y. Org. Lett. 2008, 10, 4231. doi: 10.1021/ol801605w
34. [34]
  Zhao, B.; Du, H.; Shi, Y. J. Org. Chem. 2009, 74, 8392. doi: 10.1021/jo901685c
35. [35]
  Williamson, K. S.; Yoon, T. P. J. Am. Chem. Soc. 2010, 132, 4570. doi: 10.1021/ja1013536
36. [36]
  Williamson, K. S.; Yoon, T. P. J. Am. Chem. Soc. 2012, 134, 12370. doi: 10.1021/ja3046684
37. [37]
  (a) Llaveria, J.; Beltrán, Á.; Díaz-Requejo, M. M.; Matheu, M. I.; Castillón, S.; Pérez, P. J. Angew. Chem. Int. Ed. 2010, 49, 7092.
  (b) Llaveria, J.; Beltrán, Á.; Sameera, W. M. C.; Locati, A.; Díaz-Requejo, M. M.; Matheu, M. I.; Castillón, S.; Maseras, F.; Pérez, P. J. J. Am. Chem. Soc. 2014, 136, 5342.
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
5. [5]
  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
6. [6]
  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
7. [7]
  Bizhu Shao , Huijun Dong , Yunnan Gong , Jianhua Mei , Fengshi Cai , Jinbiao Liu , Dichang Zhong , Tongbu Lu . Metal-Organic Framework-Derived Nickel Nanoparticles for Efficient CO₂ Electroreduction in Wide Potential Windows. Acta Physico-Chimica Sinica, 2024, 40(4): 2305026-0. doi: 10.3866/PKU.WHXB202305026
8. [8]
  Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291
9. [9]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
10. [10]
  Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO₂-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067
11. [11]
  Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046
12. [12]
  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
13. [13]
  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
14. [14]
  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 . Pt Single-Atom-Functionalized 2D Al-TCPP MOF Nanosheets for Enhanced Photodynamic Antimicrobial Therapy. Acta Physico-Chimica Sinica, 2025, 41(5): 100046-0. doi: 10.1016/j.actphy.2025.100046
15. [15]
  You Wu , Chang Cheng , Kezhen Qi , Bei Cheng , Jianjun Zhang , Jiaguo Yu , Liuyang Zhang . ZnO/D-A共轭聚合物S型异质结高效光催化产H₂O₂及其电荷转移动力学研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406027-. doi: 10.3866/PKU.WHXB202406027
16. [16]
  Yaping ZHANG , Tongchen WU , Yun ZHENG , Bizhou LIN . Z-scheme heterojunction β-Bi₂O₃ pillared CoAl layered double hydroxide nanohybrid: Fabrication and photocatalytic degradation property. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 531-539. doi: 10.11862/CJIC.20240256
17. [17]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
18. [18]
  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
19. [19]
  Runhua Chen , Qiong Wu , Jingchen Luo , Xiaolong Zu , Shan Zhu , Yongfu Sun . Defective Ultrathin Two-Dimensional Materials for Photo-/Electrocatalytic CO₂ Reduction: Fundamentals and Perspectives. Acta Physico-Chimica Sinica, 2025, 41(3): 2308052-0. doi: 10.3866/PKU.WHXB202308052
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(63)
Abstract views(3349)
HTML views(708)

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