Citation: Wu Dunqi, Cheng Xuan, Liu Yankai, Cheng Guo, Guan Xiaoyu, Deng Qinghai. A New Class of Chiral Pincer-Type PNN Ligands for Pd-Catalyzed Asymmetric Allylic Alkylation[J]. Chinese Journal of Organic Chemistry, ;2020, 40(10): 3362-3370. doi: 10.6023/cjoc202005090 shu

A New Class of Chiral Pincer-Type PNN Ligands for Pd-Catalyzed Asymmetric Allylic Alkylation

The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, Shanghai 200234

Corresponding author: Deng Qinghai, qinghaideng@shnu.edu.cn
Received Date: 30 May 2020
Revised Date: 16 June 2020
Available Online: 8 July 2020
Fund Project: the Shanghai Engineering Research Center of Green Energy Chemical Engineering 18DZ2254200the National Natural Science Foundation of China 21772122Project supported by the National Natural Science Foundation of China (Nos. 21402119, 21772122) and the Shanghai Engineering Research Center of Green Energy Chemical Engineering (No. 18DZ2254200)the National Natural Science Foundation of China 21402119

Figures(2)

tridentate P, N, N-donor pincer ligands bearing two or three stereocenters, 1-(4, 5-dihydro-oxazol-2-yl)-N-(2-(diphenylphosphanyl)benzyl)methanamines (oxpma), were synthesized starting from readily available amino acids in five or six steps. They were applied in palladium-catalyzed asymmetric allylic alkylation of allylic acetates to afford the desired products with high enantioselectivities (up to 96% ee).
- PNN ligand,
- pincer ligand,
- asymmetric catalysis,
- asymmetric allylic alkylation
1. [1]
  For selected books and reviewes on chiral pincer ligands, see: (a) Liu, J.-K.; Gong, J.-F.; Song, M.-P. Org. Biomol. Chem. 2019, 17, 6069.
  (b) Morales-Morales, D. Pincer Compounds: Chemistry and Applications, Elsevier, Amsterdam, 2018.
  (c) Asay, M.; Morales-Morales, D. Dalton Trans. 2015, 44, 17432.
  (d) Deng, Q.-H.; Melen, R. L.; Gade, L. H. Acc. Chem. Res. 2014, 47, 3162.
  (e) Szabó, K. L.; Wendt, O. F. Pincer and Pincer-Type Complexes, Wiley-VCH, Weinheim, 2014.
2. [2]
  (a) Hua, Y.-Y.; Bin, H.-Y.; Wei, T.; Cheng, H.-A.; Lin, Z.-P.; Fu, X.-F.; Li, Y.-Q.; Xie, J.-H.; Yan, P.-C.; Zhou, Q.-L. Org. Lett. 2020, 22, 818.
  (b) Gu, X.-S.; Yu, N.; Yang, X.-H.; Zhu, A.-T.; Xie, J.-H.; Zhou, Q.-L. Org. Lett. 2019, 21, 4111.
  (c) Chen, G.-Q.; Lin, B.-J.; Huang, J.-M.; Zhao, L.-Y.; Chen, Q.-S.; Jia, S.-P.; Yin, Q.; Zhang, X. J. Am. Chem. Soc. 2018, 140, 8064.
  (d) Zhang, Y.-M.; Yuan, M.-L.; Liu, W.-P.; Xie, J.-H.; Zhou, Q.-L. Org. Lett. 2018, 20, 4486.
  (e) Liu, Y.-T.; Chen, J.-Q.; Li, L.-P.; Shao, X.-Y.; Xie, J.-H.; Zhou, Q.-L. Org. Lett. 2017, 19, 3231.
  (f) Zhu, G.-L.; Zhang, X.-D.; Yang, L.-J.; Xie, J.-H.; Che, D.-Q.; Zhou, Q.-L.; Yan, P.-C.; Li, Y.-Q. Org. Process Res. Dev. 2016, 20, 81.
  (g) Yan, P.-C.; Xie, J.-H.; Zhang, X.-D.; Chen, K.; Li, Y.-Q.; Zhou, Q.-L.; Che, D.-Q. Chem. Commun. 2014, 50, 15987.
  (h) Yang, X.-H.; Wang, K.; Zhu, S.-F.; Xie, J.-H.; Zhou, Q.-L. J. Am. Chem. Soc. 2014, 136, 17426.
  (i) Yang, X.-H.; Xie, J.-H.; Zhou, Q.-L. Org. Chem. Front. 2014, 1, 190.
  (j) Yan, P.-C.; Zhu, G.-L.; Xie, J.-H.; Zhang, X.-D.; Zhou, Q.-L.; Li, Y.-Q.; Shen, W.-H.; Che, D.-Q. Org. Process Res. Dev. 2013, 17, 307.
  (k) Zhang, Q.-Q.; Xie, J.-H.; Yang, X.-H.; Xie, J.-B.; Zhou, Q.-L. Org. Lett. 2012, 14, 6158.
  (l) Xie, J.-H.; Liu, X.-Y.; Xie, J.-B.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2011, 50, 7329.
3. [3]
  Zhang, F.-H.; Wang, C.; Xie, J.-H.; Zhou, Q.-L. Adv. Synth. Catal. 2019, 361, 2832. doi: 10.1002/adsc.201900251
4. [4]
  Zhang, L.; Tang, Y.; Han, Z.; Ding, K. Angew.Chem., Int.Ed. 2019, 58, 4973. doi: 10.1002/anie.201814751
5. [5]
  (a) Yamamura, T.; Nakane, S.; Nomura, Y.; Tanaka, S.; Kitamura, M. Tetrahedron 2016, 72, 3781.
  (b) Yamamura, T.; Nakatsuka, H.; Tanaka, S.; Kitamura, M. Angew. Chem., Int. Ed. 2013, 52, 9313.
6. [6]
  (a) Ling, F.; Chen, J.; Nian, S.; Hou, H.; Yi, X.; Wu, F.; Xu, M.; Zhong, W. Synlett 2020, 31, 285.
  (b) Qin, C.; Hou, C.-J.; Liu, H.; Liu, Y.-J.; Huang, D.-Z.; Hu, X.-P. Tetrahedron Lett. 2018, 59, 719.
  (c) Widegren, M. B.; Harkness, G. J.; Slawin, A. M. Z.; Cordes, D. B.; Clarke, M. L. Angew. Chem., Int. Ed. 2017, 56, 5825.
  (d) Chen, X.-S.; Hou, C.-J.; Qin, C.; Liu, H.; Liu, Y.-J.; Huang, D.-Z.; Hu, X.-P. RSC Adv. 2017, 7, 12871.
  (e) Hou, C.-J.; Hu, X.-P. Org. Lett. 2016, 18, 5592.
  (f) Nie, H.; Zhou, G.; Wang, Q.; Chen, W.; Zhang, S. Tetrahedron: Asymmetry 2013, 24, 1567.
  (g) Yamamura, T.; Nakatsuka, H.; Tanaka, S.; Kitamura, M. Angew. Chem., Int. Ed. 2013, 52, 9313.
7. [7]
  (a) Gu, G.; Hu, Y.; Liu, S.; Dong, X.-Q.; Zhang, X. Chin. J. Org. Chem. 2020, 40, 997(in Chinese).
  (古国贤, 胡杨, 刘绍东, 董秀琴, 张绪穆, 有机化学, 2020, 40, 997.)
  (b) Gu, G.; Yang, T.; Yu, O.; Qian, H.; Wang, J.; Wen, J.; Dang, L.; Zhang, X. Org. Lett. 2017, 19, 5920.
  (c) Wu, W.; You, C.; Yin, C.; Liu, Y.; Dong, X.-Q.; Zhang, X. Org. Lett. 2017, 19, 2548.
  (d) Wu, W.; Liu, S.; Duan, M.; Tan, X.; Chen, C.; Xie, Y.; Lan, Y.; Dong, X.-Q.; Zhang, X. Org. Lett. 2016, 18, 2938.
8. [8]
  (a) Demmans, K. Z.; Olson, M. E.; Morris, R. H. Organometallics 2018, 37, 4608.
  (b) Díaz-Valenzuela, M. B.; Phillips, S. D.; France, M. B.; Gunn, M. E.; Clarke, M. L. Chem.-Eur. J. 2009, 15, 1227.
9. [9]
  Liu, H.; Yuan, H.; Shi, X. Dalton Trans. 2019, 48, 609. doi: 10.1039/C8DT04413A
10. [10]
  (a) Blasius, C. K.; Ren, B.-T.; Bürgy, D.; Liu, Y.-K.; Li, B.; Michalsky, I.; Wadepohl, H.; Deng, Q.-H.; Gade, L. H. J. Org. Chem. 2020, 85, 6719.
  (b) Wang, C.-J.; Sun, J.; Zhou, W.; Xue, J.; Ren, B.-T.; Zhang, G.-Y.; Mei, Y.-L.; Deng, Q.-H. Org. Lett. 2019, 21, 7315.
  (c) Bleith, T.; Deng, Q.-H.; Wadepohl, H.; Gade, L. H. Angew. Chem., Int. Ed. 2016, 55, 7852.
  (d) Deng, Q.-H.; Rettenmeier, C.; Wadepohl, H.; Gade, L. H. Chem.-Eur. J. 2014, 20, 93.
  (e) Deng, Q.-H.; Bleith, T.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2013, 135, 5356.
  (f) Deng, Q.-H.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2012, 134, 2946.
  (g) Deng, Q.-H.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2012, 134, 10769.
  (h) Deng, Q.-H.; Wadepohl, H.; Gade, L. H. Chem.-Eur. J. 2011, 17, 14922.
11. [11]
  For selected reviewes on chiral oxazoline-containing ligands, see: (a) Liu, X.; Chen, P.; Wu, F. Chin. J. Org. Chem. 2016, 36, 1797(in Chinese).
  (刘小建, 陈品红, 吴范宏, 有机化学, 2016, 36, 1797.)
  (b) Liu, L.; Ma, H.; Wu, Y.; Yuan, D.; Liu, J.; Fu, B.; Ma, X. Chin. J. Org. Chem. 2013, 33, 2283(in Chinese).
  (刘磊, 麻红利, 吴燕华, 袁德凯, 刘吉平, 傅滨, 马晓东, 有机化学, 2013, 33, 2283.)
  (c) Desimoni, G.; Faita, G.; Jørgensen, K. A. Chem. Rev. 2011, 111, PR284.
  (d) Rasappan, R.; Laventine, D.; Reiser, O. Coord. Chem. Rev. 2008, 252, 702.
  (e) McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151.
12. [12]
  For selected reviewes and examples on metal-catalyzed asymmetric allylic alkylation, see: (a) Cheng, Q.; Tu, H.-F.; Zheng, C.; Qu, J.-P.; Helmchen, G.; You, S.-L. Chem. Rev. 2019, 119, 1855.
  (b) James, J.; Jackson, M.; Guiry, P. J. Adv. Synth. Catal. 2019, 361, 3016.
  (c) Yu, F.-L.; Bai, D.-C.; Liu, X.-Y.; Jiang, Y.-J.; Ding, C.-H.; Hou, X.-L. ACS Catal. 2018, 8, 3317.
  (d) Farkas, G.; Császár, Z.; Stágel, K.; Nemes, E.; Balogh, S.; Tóth, I.; Bényei, A.; Lendvay, G.; Bakos, J. J. Organomet. Chem. 2017, 846, 129.
  (e) Jiang, Y.-J.; Zhang, G.-P.; Huang, J.-Q.; Chen, D.; Ding, C.-H.; Hou, X.-L. Org. Lett. 2017, 19, 5932.
  (f) Zheng, N.; Song, W. Chin. J. Org. Chem. 2017, 37, 1099(in Chinese).
  (郑楠, 宋汪泽, 有机化学, 2017, 37, 1099.)
  (g) Fu, J.; Huo, X.; Li, B.; Zhang, W. Org. Biomol. Chem. 2017, 15, 9747.
  (h) Hethcox, J. C.; Shockley, S. E.; Stoltz, B. M. ACS Catal. 2016, 6, 6207.
  (i) Bai, D.-C.; Yu, F.-L.; Wang, W.-Y.; Chen, D.; Li, H.; Liu, Q.-R.; Ding, C.-H.; Chen, B.; Hou, X.-L. Nat. Commun. 2016, 7, 11806.
  (j) Bai, D.-C.; Wang, W.-Y.; Ding, C.-H.; Hou, X.-L. Synlett 2015, 26, 1510.
  (k) Zhuo, C.-X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2014, 47, 2558.
  (l) Ding, C.-H.; Hou, X.-L. Top. Organomet. Chem. 2011, 36, 247.
  (m) You, S.-L.; Dai, L.-X. Angew. Chem., Int. Ed. 2006, 45, 5246.
  (n) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
13. [13]
  Singh, S. P.; Michaelides, A.; Merrill, A. R.; Schwan, A. L. J. Org. Chem. 2011, 76, 6825. doi: 10.1021/jo2008093
14. [14]
  Qi, M.-H.; Wang, F.-J.; Shi, M. Tetrahedron:Asymmetry 2010, 21, 247. doi: 10.1016/j.tetasy.2010.02.003
15. [15]
  Li, X.; Taechalertpaisarn, J.; Xin, D.; Burgess, K. Org. Lett. 2015, 17, 632. doi: 10.1021/ol5036547
16. [16]
  (a) Miao, C.; Wang, B.; Wang, Y.; Xia, C.; Lee, Y.-M.; Nam, W.; Sun, W. J. Am. Chem. Soc. 2016, 138, 936.
  (b) Steinig, A. G.; Spero, D. M. J. Org. Chem. 1999, 64, 2406.
17. [17]
  Wang, Y.; Du, S.; Armstrong, D. W. Anal. Bioanal. Chem. 2018, 410, 4725. doi: 10.1007/s00216-018-0901-5
18. [18]
  Gagnon, D.; Lauzon, S.; Godbout, C.; Spino, C. Org. Lett. 2005, 7, 4769. doi: 10.1021/ol052034n
19. [19]
  Lee, J.-Y.; Miller, J. J.; Hamilton, S. S.; Sigman, M. S. Org. Lett. 2005, 7, 1837. doi: 10.1021/ol050528e
20. [20]
  Jung, B.; Kang, S. H. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 1471. doi: 10.1073/pnas.0607865104
21. [21]
  Cheng, H.-G.; Feng, B.; Chen, L.-Y.; Guo, W.; Yu, X.-Y.; Lu, L.-Q.; Chen, J.-R.; Xiao, W.-J. Chem. Commun. 2014, 50, 2873. doi: 10.1039/C3CC49488H
22. [22]
  Jayakumar, S.; Prakash, M.; Balaraman, K.; Kesavan, V. Eur. J. Org. Chem. 2014, 606.
23. [23]
  Hao, X.-Q.; Dong, Y.-N.; Gao, B.; Li, K.; Zhao, X.-M.; Xu, Y.; Song, M.-P. Tetrahedron:Asymmetry 2015, 26, 1360. doi: 10.1016/j.tetasy.2015.10.007
24. [24]
  Jin, Y.; Du, D.-M. Tetrahedron 2012, 68, 3633 doi: 10.1016/j.tet.2012.02.078
25. [25]
  Xu, J.-X.; Ye, F.; Bai, X.-F.; Zhang, J.; Xu, Z.; Zheng, Z.-J.; Xu, L.-W. RSC Adv. 2016, 6, 45495. doi: 10.1039/C6RA09657C
1. [1]
  Yuanjin Chen , Xianghui Shi , Dajiang Huang , Junnian Wei , Zhenfeng Xi . Synthesis and reactivity of cobalt dinitrogen complex supported by nonsymmetrical pincer ligand. Chinese Chemical Letters, 2024, 35(7): 109292-. doi: 10.1016/j.cclet.2023.109292
2. [2]
  Guang Xu , Cuiju Zhu , Xiang Li , Kexin Zhu , Hao Xu . Copper-catalyzed asymmetric [4+1] annulation of yne–allylic esters with pyrazolones. Chinese Chemical Letters, 2025, 36(4): 110114-. doi: 10.1016/j.cclet.2024.110114
3. [3]
  Jieshuai Xiao , Yuan Zheng , Yue Zhao , Zhuangzhi Shi , Minyan Wang . Asymmetric Nozaki-Hiyama-Kishi (NHK)-type reaction of isatins with aromatic iodides by cobalt catalysis. Chinese Chemical Letters, 2025, 36(5): 110243-. doi: 10.1016/j.cclet.2024.110243
4. [4]
  Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
5. [5]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
6. [6]
  Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
7. [7]
  Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
8. [8]
  Luyao Lu , Chen Zhu , Fei Li , Pu Wang , Xi Kang , Yong Pei , Manzhou Zhu . Ligand effects on geometric structures and catalytic activities of atomically precise copper nanoclusters. Chinese Journal of Structural Chemistry, 2024, 43(10): 100411-100411. doi: 10.1016/j.cjsc.2024.100411
9. [9]
  Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
10. [10]
  Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
11. [11]
  Yanxin Jiang , Kwai Wun Cheng , Zhiping Yang , Jun (Joelle) Wang . Pd-catalyzed enantioselective and regioselective asymmetric hydrophosphorylation and hydrophosphinylation of enynes. Chinese Chemical Letters, 2025, 36(5): 110231-. doi: 10.1016/j.cclet.2024.110231
12. [12]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
13. [13]
  Tiantian Gong , Yanan Chen , Shuo Wang , Miao Wang , Junwei Zhao . Rigid-flexible-ligand-ornamented lanthanide-incorporated selenotungstates and photoluminescence properties. Chinese Journal of Structural Chemistry, 2024, 43(9): 100370-100370. doi: 10.1016/j.cjsc.2024.100370
14. [14]
  Ziyi Liu , Xunying Liu , Lubing Qin , Haozheng Chen , Ruikai Li , Zhenghua Tang . Alkynyl ligand for preparing atomically precise metal nanoclusters: Structure enrichment, property regulation, and functionality enhancement. Chinese Journal of Structural Chemistry, 2024, 43(11): 100405-100405. doi: 10.1016/j.cjsc.2024.100405
15. [15]
  Zhibin Ren , Shan Li , Xiaoying Liu , Guanghao Lv , Lei Chen , Jingli Wang , Xingyi Li , Jiaqing Wang . Penetrating efficiency of supramolecular hydrogel eye drops: Electrostatic interaction surpasses ligand-receptor interaction. Chinese Chemical Letters, 2024, 35(11): 109629-. doi: 10.1016/j.cclet.2024.109629
16. [16]
  Peipei CUI , Xin LI , Yilin CHEN , Zhilin CHENG , Feiyan GAO , Xu GUO , Wenning YAN , Yuchen DENG . Transition metal coordination polymers with flexible dicarboxylate ligand: Synthesis, characterization, and photoluminescence property. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2221-2231. doi: 10.11862/CJIC.20240234
17. [17]
  Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
18. [18]
  Jumei Zhang , Ziheng Zhang , Gang Li , Hongjin Qiao , Hua Xie , Ling Jiang . Ligand-mediated reactivity in CO oxidation of yttrium-nickel monoxide carbonyl complexes. Chinese Chemical Letters, 2025, 36(2): 110278-. doi: 10.1016/j.cclet.2024.110278
19. [19]
  Yongsheng Xu , Lisha Yao , Jian Li , Yanzhao Dong , Dongyang Xie , Miaomiao Zhang , Feng Li , Yunsheng Dai , Jinli Zhang , Haiyang Zhang . Dual-ligand engineering over Au-based catalyst for efficient acetylene hydrochlorination. Chinese Chemical Letters, 2025, 36(3): 110318-. doi: 10.1016/j.cclet.2024.110318
20. [20]
  He Yao , Wenhao Ji , Yi Feng , Chunbo Qian , Chengguang Yue , Yue Wang , Shouying Huang , Mei-Yan Wang , Xinbin Ma . Copper-catalyzed and biphosphine ligand controlled 3,4-boracarboxylation of 1,3-dienes with carbon dioxide. Chinese Chemical Letters, 2025, 36(4): 110076-. doi: 10.1016/j.cclet.2024.110076

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(970)
HTML views(154)

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