Citation: Xu Qing-Song, Li Chen, Xu Yong, Xu Defeng, Shen Mei-Hua, Xu Hua-Dong. Ruthenium catalyzed amination cyclization of 1, 2, 4-butanetriol with primary amines: A borrowing hydrogen strategy for 3-pyrrolidinol synthesis[J]. Chinese Chemical Letters, ;2020, 31(1): 103-106. doi: 10.1016/j.cclet.2019.05.027 shu

Ruthenium catalyzed amination cyclization of 1, 2, 4-butanetriol with primary amines: A borrowing hydrogen strategy for 3-pyrrolidinol synthesis

School of Pharmaceutical Engineering & Life Science, Changzhou University, Changzhou 213164, China

shenmh@cczu.edu.cn

hdxu@cczu.edu.cn

Received Date: 6 March 2019
Revised Date: 30 April 2019
Accepted Date: 15 May 2019
Available Online: 15 January 2019

Figures(4)

A ruthenium based catalytic system ([Ru(p-cymene)Cl₂]₂/XantPhos with substoichiometric Cs₂CO₃) has been established to effectively achieve the first direct amination cyclization of 1, 2, 4-butanetriol with primary aromatic amines. The product of this sustainable hydrogen autotransfer process is valuable Naryl-3-pyrrolidinol.
- Amination cyclization,
- N-Alkylation,
- 1, 2, 4-Butanetriol,
- 3-Pyrrolidinol,
- Borrowing hydrogen,
- Hydrogen autotransfer,
- [Ru(p-cymene)Cl₂]₂
1. [1]
  (a) T. Irrgang, R. Kempe, Chem. Rev. 119 (2019) 2524-2549;
  (b) A. Corma, J. Navas, M.J. Sabater, Chem. Rev. 118 (2018) 1410-1459;
  (c) X. Ma, C. Su, Q. Xu, Top. Curr. Chem. 374 (2016) 1-74;
  (d) Q. Yang, Q. Wang, Z. Yu, Chem. Soc. Rev. 44 (2015) 2305-2329.
2. [2]
  (a) S. Whitney, R. Grigg, A. Derrick, A. Keep, Org. Lett. 9 (2007) 3299-3302;
  (b) C. Loefberg, R. Grigg, M.A. Whittaker, A. Keep, A. Derrick, J. Org. Chem. 71 (2006) 8023-8027;
  (c) R. Grigg, T.R.B. Mitchell, S. Sutthivaiyakit, N. Tongpenyai, Chem. Commun. (1981) 611-612.
3. [3]
  Y. Watanabe, Y. Tsuji, Y. Ohsugi, Tetrahedron Lett. 22 (1981) 2667-2670. doi: 10.1016/S0040-4039(01)92965-X
4. [4]
  (a) S. Elangovan, J. Neumann, J.B. Sortais, et al., Nat. Commun. 7 (2016) 12641;
  (b) S. Baehn, S. Imm, K. Mevius, et al., Chem. Eur. J. 16 (2010) 3590-3593;
  (c) S. Imm, S. Baehn, L. Neubert, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 49 (2010) 8126-8129.
5. [5]
  (a) R. Kawahara, K.I. Fujita, R. Yamaguchi, Adv. Synth. Catal. 353 (2011) 1161-1168;
  (b) R. Kawahara, K.I. Fujita, R. Yamaguchi, J. Am. Chem. Soc. 132 (2010) 15108-15111.
6. [6]
  (a) O. Saidi, A.J. Blacker, M.M. Farah, S.P. Marsden, J.M.J. Williams, Chem. Commun. 46 (2010) 1541-1543;
  (b) O. Saidi, A.J. Blacker, G.W. Lamb, et al., Org. Process Res. Dev. 14 (2010) 1046-1049.
7. [7]
  (a) R. Martinez, D.J. Ramon, M. Yus, Org. Biomol. Chem. 7 (2009) 2176-2181;
  (b) R. Martinez, G.J. Brand, D.J. Ramon, M. Yus, Tetrahedron Lett. 46 (2005) 3683-3686.
8. [8]
  (a) S. Michlik, R. Kempe, Chem. Eur. J. 16 (2010) 13193-13198;
  (b) B. Blank, R. Kempe, J. Am. Chem. Soc. 132 (2010) 924-925.
9. [9]
  C. Gunanathan, D. Milstein, Angew. Chem. Int. Ed. 47 (2008) 8661-8664. doi: 10.1002/anie.200803229
10. [10]
  (a) S. Liu, R. Chen, G.J. Deng, Chem. Lett. 40 (2011) 489-491;
  (b) Y. Liu, W. Chen, C. Feng, G. Deng, Chem. Asian J. 6 (2011) 1142-1146.
11. [11]
  S.L. Feng, C.Z. Liu, Q. Li, X.C. Yu, Q. Xu, Chin. Chem. Lett. 22 (2011) 1021-1024. doi: 10.1016/j.cclet.2011.03.014
12. [12]
  (a) X. Cui, F. Shi, Y. Zhang, Y. Deng, Tetrahedron Lett. 51 (2010) 2048-2051;
  (b) X. Cui, F. Shi, M.K. Tse, et al., Adv. Synth. Catal. 351 (2009) 2949-2958.
13. [13]
  (a) B. Emayavaramban, P. Chakraborty, E. Manoury, R. Poli, B. Sundararaju, Org. Chem. Front. 6 (2019) 852-857;
  (b) C.M. Hsiao, Y.F. Chen, C.H. Lin, et al., J. Organomet. Chem. 861 (2018) 10-16;
  (c) G. Zhang, Z. Yin, S. Zheng, Org. Lett. 18 (2016) 300-303;
  (d) T. Yan, B.L. Feringa, K. Barta, ACS Catal. 6 (2016) 381-388;
  (e) Q. Zou, C. Wang, J. Smith, D. Xue, J. Xiao, Chem. Eur. J. 21 (2015) 9656-9661;
  (f) Y. Zhang, X. Qi, X. Cui, F. Shi, Y. Deng, Tetrahedron Lett. 52 (2011) 1334-1338;
  (g) J.Y. Zhang, X. Huang, Q.Y. Shen, J.Y. Wang, G.H. Song, Chin. Chem. Lett. 29 (2018) 197-200;
  (h) T.T. Zhang, J.Y. Jiang, Y.H. Wang, Chin. Chem. Lett. 28 (2017) 307-311.
14. [14]
  C. Gunanathan, D. Milstein, Science 341 (2013) 249.
15. [15]
  (a) J. Leonard, A.J. Blacker, S.P. Marsden, et al., Org. Process Res. Dev. 19 (2015) 1400-1410;
  (b) M.A. Berliner, S.P.A. Dubant, T. Makowski, et al., Org. Process Res. Dev. 15 (2011) 1052-1062.
16. [16]
  (a) T. Yan, B.L. Feringa, K. Barta, Nat. Commun. 5 (2014) 5602;
  (b) A.B. Enyong, B. Moasser, J. Org. Chem. 79 (2014) 7553-7563;
  (c) G. Cami-Kobeci, J.M.J. Williams, Chem. Commun. (2004) 1072-1073;
  (d) X. Cui, X. Dai, Y. Deng, F. Shi, Chem. Eur. J. 19 (2013) 3665-3675;
  (e) A. Wetzel, S. Woeckel, M. Schelwies, et al., Org. Lett. 15 (2013) 266-269;
  (f) M.H.S.A. Hamid, C.L. Allen, G.W. Lamb, et al., J. Am. Chem. Soc. 131 (2009) 1766-1774;
  (g) I. Yamaguchi, T. Sakano, H. Ishii, K. Osakada, T. Yamamoto, J. Organomet. Chem. 584 (1999) 213-216;
  (h) D. Seyferth, R.C. Hui, J. Org. Chem. 50 (1985) 1985-1987;
  (i) L.Y. Xie, S. Peng, L.L. Jiang, et al., Org. Chem. Front. 6 (2019) 167-171.
17. [17]
  (a) A.J.A. Watson, A.C. Maxwell, J.M.J. Williams, J. Org. Chem. 76 (2011) 2328-2331;
  (b) R.A.T.M. Abbenhuis, J. Boersma, G. van Koten, J. Org. Chem. 63 (1998) 4282-4290.
18. [18]
  (a) K.O. Marichev, J.M. Takacs, ACS Catal. 6 (2016) 2205-2210;
  (b) K.I. Fujita, T. Fujii, R. Yamaguchi, Org. Lett. 6 (2004) 3525-3528.
19. [19]
  (a) J. Katz, J. Jewell, J. Jung, et al., PT: WO2010017047A1, 2010;
  (b) G.M. Bright, PT: WO9952907A1, 1999;
  (c) A. Naylor, D.B. Judd, D.I.C. Scopes, A.G. Hayes, P.J. Birch, J. Med. Chem. 37 (1994) 2138-2144;
  (d) L. Li, Q. Chen, X. Xiong, et al., Chin. Chem. Lett. 29 (2018) 1893-1896.
20. [20]
  (a) K. Zong, Bull. Korean Chem. Soc. 26 (2005) 717-718;
  (b) E.J. Trybulski, R.H. Kramss, R.M. Mangano, H.J. Brabander, G. Francisco, Bioorg. Med. Chem. Lett. 2 (1992) 827-832;
  (c) A. Dicko, M. Montury, M. Baboulene, Tetrahedron Lett. 28 (1987) 6041-6044;
  (d) M.M. Bowers Nemia, J. Lee, M.M. Joullie, Synth. Commun. 13 (1983) 1117-1123.
21. [21]
  A.J. Rawlings, L.J. Diorazio, M. Wills, Org. Lett. 17 (2015) 1086-1089. doi: 10.1021/ol503587n
1. [1]
  Xinyu Hou , Xuelian Yu , Meng Liu , Hengxing Peng , Lijuan Wu , Libing Liao , Guocheng Lv . Ultrafast synthesis of Mo₂N with highly dispersed Ru for efficient alkaline hydrogen evolution. Chinese Chemical Letters, 2025, 36(4): 109845-. doi: 10.1016/j.cclet.2024.109845
2. [2]
  Kaihui Huang , Boning Feng , Xinghua Wen , Lei Hao , Difa Xu , Guijie Liang , Rongchen Shen , Xin Li . Effective photocatalytic hydrogen evolution by Ti3C2-modified CdS synergized with N-doped C-coated Cu2O in S-scheme heterojunctions. Chinese Journal of Structural Chemistry, 2023, 42(12): 100204-100204. doi: 10.1016/j.cjsc.2023.100204
3. [3]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
4. [4]
  Liyong Ding , Zhenhua Pan , Qian Wang . 2D photocatalysts for hydrogen peroxide synthesis. Chinese Chemical Letters, 2024, 35(12): 110125-. doi: 10.1016/j.cclet.2024.110125
5. [5]
  Xinlong Zheng , Zhongyun Shao , Jiaxin Lin , Qizhi Gao , Zongxian Ma , Yiming Song , Zhen Chen , Xiaodong Shi , Jing Li , Weifeng Liu , Xinlong Tian , Yuhao Liu . Recent advances of CuSbS₂ and CuPbSbS₃ as photocatalyst in the application of photocatalytic hydrogen evolution and degradation. Chinese Chemical Letters, 2025, 36(3): 110533-. doi: 10.1016/j.cclet.2024.110533
6. [6]
  Ke Wang , Jia Wu , Shuyi Zheng , Shibin Yin . NiCo Alloy Nanoparticles Anchored on Mesoporous Mo2N Nanosheets as Efficient Catalysts for 5-Hydroxymethylfurfural Electrooxidation and Hydrogen Generation. Chinese Journal of Structural Chemistry, 2023, 42(10): 100104-100104. doi: 10.1016/j.cjsc.2023.100104
7. [7]
  Zhen Shi , Wei Jin , Yuhang Sun , Xu Li , Liang Mao , Xiaoyan Cai , Zaizhu Lou . Interface charge separation in Cu2CoSnS4/ZnIn2S4 heterojunction for boosting photocatalytic hydrogen production. Chinese Journal of Structural Chemistry, 2023, 42(12): 100201-100201. doi: 10.1016/j.cjsc.2023.100201
8. [8]
  Fei Jin , Bolin Yang , Xuanpu Wang , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Facilitating efficient photocatalytic hydrogen evolution via enhanced carrier migration at MOF-on-MOF S-scheme heterojunction interfaces through a graphdiyne (CnH2n-2) electron transport layer. Chinese Journal of Structural Chemistry, 2023, 42(12): 100198-100198. doi: 10.1016/j.cjsc.2023.100198
9. [9]
  Ping Lu , Baoyin Du , Ke Liu , Ze Luo , Abiduweili Sikandaier , Lipeng Diao , Jin Sun , Luhua Jiang , Yukun Zhu . Heterostructured In2O3/In2S3 hollow fibers enable efficient visible-light driven photocatalytic hydrogen production and 5-hydroxymethylfurfural oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100361-100361. doi: 10.1016/j.cjsc.2024.100361
10. [10]
  Minying Wu , Xueliang Fan , Wenbiao Zhang , Bin Chen , Tong Ye , Qian Zhang , Yuanyuan Fang , Yajun Wang , Yi Tang . Highly dispersed Ru nanospecies on N-doped carbon/MXene composite for highly efficient alkaline hydrogen evolution. Chinese Chemical Letters, 2024, 35(4): 109258-. doi: 10.1016/j.cclet.2023.109258
11. [11]
  Guixu Pan , Zhiling Xia , Ning Wang , Hejia Sun , Zhaoqi Guo , Yunfeng Li , Xin Li . Preparation of high-efficient donor-π-acceptor system with crystalline g-C3N4 as charge transfer module for enhanced photocatalytic hydrogen evolution. Chinese Journal of Structural Chemistry, 2024, 43(12): 100463-100463. doi: 10.1016/j.cjsc.2024.100463
12. [12]
  Wen-Tao Ouyang , Jun Jiang , Yan-Fang Jiang , Ting Li , Yuan-Yuan Liu , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038
13. [13]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
14. [14]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
15. [15]
  Linfang ZHANG , Wenzhu YIN , Gui YIN . A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 540-548. doi: 10.11862/CJIC.20240405
16. [16]
  Xing Xiao , Yunling Jia , Wanyu Hong , Yuqing He , Yanjun Wang , Lizhi Zhao , Huiqin An , Zhen Yin . Sulfur-defective ZnIn2S4 nanosheets decorated by TiO2 nanosheets with exposed {001} facets to accelerate charge transfer for efficient photocatalytic hydrogen evolution. Chinese Journal of Structural Chemistry, 2024, 43(12): 100474-100474. doi: 10.1016/j.cjsc.2024.100474
17. [17]
  Jiao Li , Chenyang Zhang , Chuhan Wu , Yan Liu , Xuejian Zhang , Xiao Li , Yongtao Li , Jing Sun , Zhongmin Su . Defined organic-octamolybdate crystalline superstructures derived Mo₂C@C as efficient hydrogen evolution electrocatalysts. Chinese Chemical Letters, 2024, 35(6): 108782-. doi: 10.1016/j.cclet.2023.108782
18. [18]
  Pingping HAO , Fangfang LI , Yawen WANG , Houfen LI , Xiao ZHANG , Rui LI , Lei WANG , Jianxin LIU . Hydrogen production performance of the non-platinum-based MoS₂/CuS cathode in microbial electrolytic cells. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1811-1824. doi: 10.11862/CJIC.20240054
19. [19]
  Shuanglin TIAN , Tinghong GAO , Yutao LIU , Qian CHEN , Quan XIE , Qingquan XIAO , Yongchao LIANG . First-principles study of adsorption of Cl₂ and CO gas molecules by transition metal-doped g-GaN. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1189-1200. doi: 10.11862/CJIC.20230482
20. [20]
  Yan Cheng , Hua-Peng Ruan , Yan Peng , Longhe Li , Zhenqiang Xie , Lang Liu , Shiyong Zhang , Hengyun Ye , Zhao-Bo Hu . Magnetic, dielectric and luminescence synergetic switchable effects in molecular material [Et₃NCH₂Cl]₂[MnBr₄]. Chinese Chemical Letters, 2024, 35(4): 108554-. doi: 10.1016/j.cclet.2023.108554

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(1033)
HTML views(89)

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