Citation: Zhao Ran, Feng Guidong, Xin Xiaodong, Guan Honghao, Hua Jing, Wan Renzhong, Li Wei, Liu Lei. Oxidative C-H alkynylation of 3, 6-dihydro-2H-pyrans[J]. Chinese Chemical Letters, ;2019, 30(7): 1432-1434. doi: 10.1016/j.cclet.2019.03.027 shu

Oxidative C-H alkynylation of 3, 6-dihydro-2H-pyrans

Zhao Ran ^a ,
Feng Guidong ^b ,
Xin Xiaodong ^c ,
Guan Honghao ^c ,
Hua Jing ^d ,
Wan Renzhong ^b,*, ,
Li Wei ^a,*, ,
Liu Lei ^c,*,

a.
Department of Pharmaceutical Analysis, School of Pharmacy, Shandong University of Traditional Chinese Medicine, Ji'nan 250355, China
b.
College of Animal Science and Veterinary Medicine, Shandong Agricultural University, Taian 271018, China
c.
School of Chemistry and Chemical Engineering, Shandong University, Ji'nan 250100, China
d.
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, China

wrzh63@163.com

liwei6911@163.com

leiliu@sdu.edu.cn

Received Date: 23 February 2019
Revised Date: 12 March 2019
Accepted Date: 18 March 2019
Available Online: 19 July 2019

Figures(6)

Current synthesis of α-substituted 3, 6-dihydro-2H-pyrans dominantly relies on functional group transformation. Herein, a direct and practical oxidative C-H alkynylation and alkenylation of 3, 6-dihydro-2H-pyran skeletons with a range of potassium trifluoroborates is developed. The metal-free process is well tolerated with a wide variety of 3, 6-dihydro-2H-pyrans, rapidly providing a library of 2, 4-disubstituted 3, 6-dihydro-2H-pyrans with diverse patterns of α-functionalities for further diversification and bioactive small molecule identification.
- 3, 6-Dihydro-2H-pyrans,
- C-H Functionalization,
- Alkynylation,
- Oxidation,
- Organoborane
1. [1]
  (a) M.M. Faul, B.E. Huff, Chem. Rev. 100 (2000) 2407-2474;
  (b) E.J. Kang, E. Lee, Chem. Rev. 105 (2005) 4348-4378;
  (c) T. Nakata, Chem. Rev. 105 (2005) 4314-4347;
  (d) S.D. Roughley, A.M. Jordan, J. Med. Chem. 54 (2011) 3451-3479;
  (e) L.G. León, P.O. Miranda, V.S. Martín, J.I. Padrón, J.M. Padrón, Bioorg. Med. Chem. Lett. 17 (2007) 3087-3090;
  (f) T.A. Johnson, K. Tenney, R.H. Cichewicz, et al., J. Med. Chem. 50 (2007) 3795-3803;
  (g) J. De Pascual Teresa, S. Vincente, M.S. Gonzalez, I.S. Bellido, Phytochemistry 22 (1983) 2235-2238.
2. [2]
  (a) P.O. Miranda, D.D. Díaz, J.I. Padrón, J. Bermejo, V.S. Martín, Org. Lett. 5 (2003) 1979-1982;
  (b) P.O. Miranda, R.M. Carballo, V.S. Martín, J.I. Padrón, Org. Lett. 11 (2009) 357-360;
  (c) Y. Lian, R.J. Hinkle, J. Org. Chem. 71 (2006) 7071-7074.
3. [3]
  (a) T.L. Gresham, T.R. Steadman, J. Am. Chem. Soc. 71 (1 949) 737-738;
  (b) K. Fujiwara, T. Kurahashi, S. Matsubara, J. Am. Chem. Soc. 134 (2012) 5512-5515;
  (c) L. Liu, H. Kim, Y. Xie, et al., J. Am. Chem. Soc. 139 (2017) 13656-13659.
4. [4]
  (a) B.M. Trost, B.S. Brown, E.J. McEachern, O. Kuhn, Chem.-Eur. J. 9 (2003) 4442-4451;
  (b) S. Basu, H. Waldmann, J. Org. Chem. 71 (2006) 3977-3979.
5. [5]
  (a) W. Kong, J. Cui, Y. Yu, et al., Org. Lett. 11 (2009) 1213-1216;
  (b) K.P. Kalbarczyk, S.T. Diver, J. Org. Chem. 74 (2009) 2193-2196;
  (c) K. Watanabe, J. Li, N. Veerasamy, A. Ghosh, R.G. Carter, Org. Lett. 18 (2016) 1744-1747;
  (d) B. Guo, G. Schwarzwalder, J.T. Njardarson, Angew. Chem. Int. Ed. 51 (2012) 5675-5678.
6. [6]
  (a) I.P. Beletskaya, A.V. Cheprakov, Chem. Rev. 100 (2000) 3009-3066;
  (b) G. Peh, P.E. Floreancig, Org. Lett. 17 (2015) 3750-3753.
7. [7]
  A.M. Gómez, F. Lobo, C. Uriel, J. Cristóbal López, Eur. J. Org. Chem. 2013(2013) 7221-7262.
8. [8]
  (a) K. Godula, D. Sames, Science 312 (2006) 67-72;
  (b) W.R. Gutekunst, P.S. Baran, Chem. Soc. Rev. 40 (2011) 1976-1991;
  (c) R. Giri, B.F. Shi, K.M. Engle, N. Maugel, J.Q. Yu, Chem. Soc. Rev. 38 (2009) 3242-3272;
  (d) J. Robertson, J. Pillai, R.K. Lush, Chem. Soc. Rev. 30 (2001) 94-103;
  (e) H.M.L. Davies, Angew. Chem. Int. Ed. 45 (2006) 6422-6425;
  (f) S.Y. Zhang, F.M. Zhang, Y.Q. Tu, Chem. Soc. Rev. 40 (2011) 1937-1 949.
9. [9]
  (a) C.J. Li, Z. Li, Pure Appl. Chem. 78 (2006) 935-945;
  (b) S. Murahashi, D. Zhang, Chem. Soc. Rev. 37 (2008) 1490-1501;
  (c) C.J. Li, Acc. Chem. Res. 42 (2009) 335-344;
  (d) C.J. Scheuermann, Chem.-Asian J. 5 (2010) 436-451;
  (e) M. Klussmann, D. Sureshkumar, Synthesis (2011) 353-369;
  (f) C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 111 (2011) 1780-1824;
  (g) C.L. Sun, B.J. Li, Z.J. Shi, Chem. Rev. 111 (2011) 1293-1314;
  (h) C. Zhang, C. Tang, N. Jiao, Chem. Soc. Rev. 41 (2012) 3464-3484;
  (i) S.H. Cho, J.Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 40 (2011) 5068-5083;
  (j) J. Le Bras, J. Muzart, Chem. Rev. 111 (2011) 1170-1214;
  (k) C.S. Yeung, V.M. Dong, Chem. Rev. 111 (2011) 1215-1292;
  (l) R. Rohlmann, O. García Mancheño, Synlett 24 (2013) 6-10;
  (m) S.A. Girard, T. Knauber, C.J. Li, Angew. Chem. Int. Ed. 53 (2014) 74-100.
10. [10]
  (a) Y. Zhang, C.J. Li, Angew. Chem. Int. Ed. 45 (2006) 1949-1952;
  (b) Y. Zhang, C.J. Li, J. Am. Chem. Soc. 128 (2006) 4242-4243;
  (c) M. Ghobrial, K. Harhammer, M.D. Mihovilovic, M. Schnürch, Chem. Commun. 46 (2010) 8836-8838;
  (d) H. Richter, R. Rohlmann, O. García Mancheño, Chem.-Eur. J. 17 (2011) 11622-11627;
  (e) S.J. Park, J.R. Price, M.H. Todd, J. Org. Chem. 77 (2012) 949-955;
  (f) D.J. Clausen, P.E. Floreancig, J. Org. Chem. 77 (2012) 6574-6582;
  (g) X. Liu, B. Sun, Z. Xie, X. Qin, L. Liu, H. Lou, J. Org. Chem. 78 (2013) 31 04-3112;
  (h) W. Chen, Z. Xie, H. Zheng, H. Lou, L. Liu, Org. Lett. 16 (2014) 5988-5991;
  (i) Z. Meng, S. Sun, H. Yuan, H. Lou, L. Liu, Angew. Chem. Int. Ed. 53 (2014) 543-547;
  (j) W. Muramatsu, K. Nakano, Org. Lett. 16 (2014) 2 042-2 045;
  (k) M. Xiang, Q.Y. Meng, X.W. Gao, et al., Org. Chem. Front. 3 (2016) 486-490;
  (l) Z. Peng, Y. Wang, Z. Yu, et al., J. Org. Chem. 83 (2018) 7900-7906;
  (m) L. Jin, J. Feng, G. Lu, C. Cai, Adv. Synth. Catal. 357 (2015) 2105-2110.
11. [11]
  P. Magnus, J. Lacour, P.A. Evans, P. Rigollier, H. Tobler, J. Am. Chem. Soc. 120(1998) 12486-12499. doi: 10.1021/ja9829564
12. [12]
  R. Zhou, H. Liu, H. Tao, X. Yu, J. Wu, Chem. Sci. 8(2017) 4654-4659. doi: 10.1039/C7SC00953D
13. [13]
  M. Wan, Z. Meng, H. Lou, L. Liu, Angew. Chem. Int. Ed. 53(2014) 13845-13849. doi: 10.1002/anie.201407083
14. [14]
  F. Diederich, P.J. Stang, R.R. Tykwinski, Acetylene Chemistry:Chemistry, Biology and Material Science, Wiley-VCH, Weinheim, 2005.
15. [15]
  H.H. Jung, P.E. Floreancig, Tetrahedron 65(2009) 10830-10836. doi: 10.1016/j.tet.2009.10.088
1. [1]
  Pengfei Zhang , Qingxue Ma , Zhiwei Jiang , Xiaohua Xu , Zhong Jin . Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template. Chinese Chemical Letters, 2024, 35(8): 109361-. doi: 10.1016/j.cclet.2023.109361
2. [2]
  Zhikang Wu , Guoyong Dai , Qi Li , Zheyu Wei , Shi Ru , Jianda Li , Hongli Jia , Dejin Zang , Mirjana Čolović , Yongge Wei . POV-based molecular catalysts for highly efficient esterification of alcohols with aldehydes as acylating agents. Chinese Chemical Letters, 2024, 35(8): 109061-. doi: 10.1016/j.cclet.2023.109061
3. [3]
  Chen Lian , Si-Han Zhao , Hai-Lou Li , Xinhua Cao . A giant Ce-containing poly(tungstobismuthate): Synthesis, structure and catalytic performance for the decontamination of a sulfur mustard simulant. Chinese Chemical Letters, 2024, 35(10): 109343-. doi: 10.1016/j.cclet.2023.109343
4. [4]
  Lei Wan , Yizhou Tong , Xi Lu , Yao Fu . Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp³) and C(sp)-C(sp²) bonds. Chinese Chemical Letters, 2024, 35(7): 109283-. doi: 10.1016/j.cclet.2023.109283
5. [5]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
6. [6]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
7. [7]
  Gang Hu , Chun Wang , Qinqin Wang , Mingyuan Zhu , Lihua Kang . The controlled oxidation states of the H₄PMo₁₁VO₄₀ catalyst induced by plasma for the selective oxidation of methacrolein. Chinese Chemical Letters, 2025, 36(2): 110298-. doi: 10.1016/j.cclet.2024.110298
8. [8]
  Bicheng Zhu , Jingsan Xu . S-scheme heterojunction photocatalyst for H2 evolution coupled with organic oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100327-100327. doi: 10.1016/j.cjsc.2024.100327
9. [9]
  Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
10. [10]
  Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2024.100416
11. [11]
  Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
12. [12]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
13. [13]
  Jian Han , Li-Li Zeng , Qin-Yu Fei , Yan-Xiang Ge , Rong-Hui Huang , Fen-Er Chen . Recent advances in remote C(sp³)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction. Chinese Chemical Letters, 2024, 35(11): 109647-. doi: 10.1016/j.cclet.2024.109647
14. [14]
  Huixin Chen , Chen Zhao , Hongjun Yue , Guiming Zhong , Xiang Han , Liang Yin , Ding Chen . Unraveling the reaction mechanism of high reversible capacity CuP₂/C anode with native oxidation PO_x component for sodium-ion batteries. Chinese Chemical Letters, 2025, 36(1): 109650-. doi: 10.1016/j.cclet.2024.109650
15. [15]
  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
16. [16]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
17. [17]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
18. [18]
  Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H₂O₂ Production and Cr(VI) Reduction over a Hierarchical Ti₃C₂/In₄SnS₈ Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
19. [19]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
20. [20]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(902)
HTML views(86)

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