Citation: Wang Zehua, Mao Ying, Guan Honghao, Cao Min, Hua Jing, Feng Lei, Liu Lei. Direct oxidative C(sp³) -H cyanation of secondary benzylic ethers[J]. Chinese Chemical Letters, ;2019, 30(6): 1241-1243. doi: 10.1016/j.cclet.2019.03.019 shu

Direct oxidative C(sp³) -H cyanation of secondary benzylic ethers

Wang Zehua ^a ,
Mao Ying ^b ,
Guan Honghao ^a ,
Cao Min ^a ,
Hua Jing ^c ,
Feng Lei ^a,*, ,
Liu Lei ^a,b,*,

a.
School of Chemistry and Chemical Engineering, Shandong University, Ji'nan 250100, China
b.
School of Pharmaceutical Sciences, Shandong University, Ji'nan 250012, China
c.
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, China

E-mail addresses:

feng_lei@sdu.edu.cn

leiliu@sdu.edu.cn

Received Date: 7 February 2019
Revised Date: 5 March 2019
Accepted Date: 12 March 2019
Available Online: 16 June 2019

Figures(4)

Current studies on the oxidative C-H functionalization of benzylic ethers for C-C forging process dominantly focus on primary ethers. The corresponding reaction of secondary ethers remains underdeveloped. Herein, a practical and efficient oxidative C-H cyanation of secondary benzylic ethers with TMSCN in the presence of DDQ is described. The metal-free process is well tolerated with a wide variety of electronically varied α-monosubstituted isochromans, facilely furnishing a library of isochromans bearing α-aryl α-cyano substituent patterns for further diversification and bioactive small molecule identification.
- C-H functionalization,
- Cyanation,
- Oxidation,
- Secondary ether,
- Tertiary ether synthesis
1. [1]
  (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) 1937-1949.
2. [2]
  (a) P.A. Wender, V.A. Verma, T.J. Paxton, T.H. Pillow, Acc. Chem. Res. 41 (2008) 40-49;
  (b) B.M. Trost, Acc. Chem. Res. 35 (2002) 695-705.
3. [3]
  (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.
4. [4]
  (a) Z. Li, C.J. Li, J. Am. Chem. Soc. 126 (2004) 11810-11811;
  (b) Z. Li, R. Yu, H. Li, Angew. Chem. Int. Ed. 47 (2008) 7497-7450;
  (c) F. Yang, J. Li, J. Xie, Z.Z. Huang, Org. Lett. 12 (2010) 5214-5217;
  (d) D.P. Hari, B. König, Org. Lett. 13 (2011) 3852-3855;
  (e) E.Boess, D.Sureshkumar, A.Sud, etal., J.Am.Chem.Soc.133 (2011) 8106-8109;
  (f) E. Boess, C. Schmitz, M. Klussmann, J. Am. Chem. Soc. 134 (2012) 5317-5325;
  (g)S.I.Murahashi, T.Nakae, H.Terai, N.Komiya, J.Am.Chem.Soc.130 (2008) 11005-11012;
  (h)S.I. Murahashi, N. Komiya, H.Terai, T.Nakae, J.Am.Chem.Soc.125 (2003) 15312-15313;
  (i) W. Muramatsu, K. Nakano, C.J. Li, Org. Lett. 15 (2013) 3650-3653;
  (j) Z. Xie, L. Liu, W. Chen, et al., Angew. Chem. Int. Ed. 53 (2014) 3904-3908;
  (k) J. Zhang, B. Tiwari, C. Xing, X. Chen, Y.R. Chi, Angew. Chem. Int. Ed. 51 (2012) 3649-3652;
  (l)G. Zhang, Y. Ma, S. Wang, Y.Zhang, R. Wang, J. Am. Chem. Soc.134 (2012) 12334-12337;
  (m) D.A. DiRocco, T. Rovis, J. Am. Chem. Soc. 134 (2012) 8094-8097;
  (n) G. Bergonzini, C.S. Schindler, C.J. Wallentin, E.N. Jacobsen, C.R.J. Stephenson, Chem. Sci. 5 (2014) 112-116;
  (o)X.Liu, Z.Meng, C.Li, H.Lou, L.Liu, Angew.Chem.Int.Ed.54 (2015)6012-6015;
  (p) X. Liu, S. Sun, Z. Meng, H. Lou, L. Liu, Org. Lett. 17 (2015) 2396-2399;
  (q) Z. Xie, X. Liu, L. Liu, Org. Lett. 18 (2016) 2982-2985;
  (r) G. Wei, C. Zhang, F. Bureš, et al., ACS Catal. 6 (2016) 3708-3712.
5. [5]
  (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) W.Y. Tu, L. Liu, P.E. Floreancig, Angew. Chem. Int. Ed. 47 (2008) 4184-4187;
  (d) L. Liu, P.E. Floreancig, Org. Lett. 11 (2009) 3152-3155;
  (e) M. Ghobrial, K. Harhammer, M.D. Mihovilovic, M. Schnürch, Chem. Commun. 46 (2010) 8836-8838;
  (f) H. Richter, R. Rohlmann, O. García Mancheño, Chem. -Eur. J. 17 (2011) 11622-11627;
  (g) M. Ghobrial, M. Schnürch, M.D. Mihovilovic, J. Org. Chem. 76 (2011) 8781-8793;
  (h) S.J. Park, J.R. Price, M.H. Todd, J. Org. Chem. 77 (2012) 949-955;
  (i) D.J. Clausen, P.E. Floreancig, J. Org. Chem. 77 (2012) 6574-6582;
  (j) X. Liu, B. Sun, Z. Xie, et al., J. Org. Chem. 78 (2013) 3104-3112;
  (k) W. Chen, Z. Xie, H. Zheng, H. Lou, L. Liu, Org. Lett. 16 (2014) 5988-5991;
  (l) Z. Meng, S. Sun, H. Yuan, H. Lou, L. Liu, Angew. Chem. Int. Ed. 53 (2014) 543-547;
  (m) W. Muramatsu, K. Nakano, Org. Lett. 16 (2014) 2042-2045;
  (n) M. Xiang, Q.Y. Meng, J.X. Li, et al., Chem. -Eur. J. 21 (2015) 18080-18084;
  (o) M. Xiang, Q.Y. Meng, X.W. Gao, et al., Org. Chem. Front. 3 (2016) 486-490;
  (p) Z. Peng, Y. Wang, Z. Yu, et al., J. Org. Chem. 83 (2018) 7900-7906;
  (q) A. Lee, R.C. Betori, E.A. Crane, K.A. Scheidt, J. Am. Chem. Soc. 140 (2018) 6212-6216;
  (r) L. Jin, J. Feng, G. Lu, C. Cai, Adv. Synth. Catal. 357 (2015) 2105-2110.
6. [6]
  L. Liu, P.E. Floreancig, Angew. Chem. Int. Ed. 49(2010) 5894-5897. doi: 10.1002/anie.201002281
7. [7]
  (a) S.D. Roughley, A.M. Jordan, J. Med. Chem. 54 (2011) 3451-3479;
  (b) Z. Lu, Z. Lin, W. Wang, et al., J. Nat. Prod. 71 (2008) 543-546;
  (c) R.E. TenBrink, C.L. Bergh, J.N. Duncan, J. Med. Chem. 39 (1996) 2435-2437;
  (d) U. Albrecht, M. Lalk, P. Langer, Bioorg. Med. Chem. 13 (2005) 1531-1536;
  (e) S. Bräse, A. Encinas, J. Keck, C.F. Nising, Chem. Rev. 109 (2009) 3903-3990;
  (f) D.R. McMullin, T.K. Nsiama, J.D. Miller, J. Nat. Prod. 77 (2014) 206-212.
8. [8]
  (a) M.B. Sommer, O. Nielsen, H. Petersen, Patent, US 2011/0065938 (2011);
  (b) T. Giridhar, G. Srinivasulu, K.S. Rao, Patent, US 2011/0092719 (2011);
  (c) N. Chinkov, A. Warm, E.M. Carreira, Angew. Chem. Int. Ed. 50 (2011) 2957-2961.
9. [9]
  (a) D. Enders, J.P. Shilvock, Chem. Soc. Rev. 29 (2000) 359-373;
  (b) F.F. Fleming, Nat. Prod. Rep. 16 (1999) 597-606;
  (c) F.F. Fleming, L. Yao, P.C. Ravikumar, L. Funk, B.C. Shook, J. Med. Chem. 53 (2010) 7902-7917.
10. [10]
  (a) S. Kamijo, T. Hoshikawa, M. Inoue, Org. Lett. 13 (2011) 5928-5931;
  (b) S. Kong, L. Zhang, X. Dai, et al., Adv. Synth. Catal. 357 (2015) 2453-2456;
  (c) C. Yan, Y. Liu, Q. Wang, RSC Adv. 4 (2014) 60075-60078;
  (d) F. Le Vaillant, T. Courant, J. Waser, Chem. Sci. 8 (2017) 1790-1800;
  (e) M.X. Sun, Y.F. Wang, B.H. Xu, X.Q. Ma, S.J. Zhang, Org. Biomol. Chem. 16 (2018) (1971);
  (f) Y. Xia, L. Wang, A. Studer, Angew. Chem. Int. Ed. 57 (2018) 12940-12944.
11. [11]
  S. Dasgupta, T. Rivas, M.P. Watson, Angew. Chem. Int. Ed. 54(2015) 14154-14158. doi: 10.1002/anie.201507373
12. [12]
  H.H. Jung, P.E. Floreancig, Tetrahedron 65(2009) 10830-10836. doi: 10.1016/j.tet.2009.10.088
1. [1]
  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
2. [2]
  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
3. [3]
  Wenling Yuan , Fengli Li , Zhe Chen , Qiaoxin Xu , Zhenhua Guan , Nanyu Yao , Zhengxi Hu , Junjun Liu , Yuan Zhou , Ying Ye , Yonghui Zhang . AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement. Chinese Chemical Letters, 2024, 35(5): 108788-. doi: 10.1016/j.cclet.2023.108788
4. [4]
  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
5. [5]
  Xiao Zhu , Yanbing Mo , Jiawei Chen , Gaopan Liu , Yonggang Wang , Xiaoli Dong . A weakly-solvated ether-based electrolyte for fast-charging graphite anode. Chinese Chemical Letters, 2024, 35(8): 109146-. doi: 10.1016/j.cclet.2023.109146
6. [6]
  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
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]
  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
9. [9]
  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
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]
  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
12. [12]
  Jingping Hu , Jing Xu . Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C₁₄–epi-deoxycalyciphylline H. Chinese Chemical Letters, 2024, 35(4): 108733-. doi: 10.1016/j.cclet.2023.108733
13. [13]
  Jun Zhang , Zhiyao Zheng , Can Zhu . Stereochemical editing: Catalytic racemization of secondary alcohols and amines. Chinese Chemical Letters, 2024, 35(5): 109160-. doi: 10.1016/j.cclet.2023.109160
14. [14]
  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
15. [15]
  Guanxiong Yu , Chengkai Xu , Huaqiang Ju , Jie Ren , Guangpeng Wu , Chengjian Zhang , Xinghong Zhang , Zhen Xu , Weipu Zhu , Hao-Cheng Yang , Haoke Zhang , Jianzhao Liu , Zhengwei Mao , Yang Zhu , Qiao Jin , Kefeng Ren , Ziliang Wu , Hanying Li . Key progresses of MOE key laboratory of macromolecular synthesis and functionalization in 2023. Chinese Chemical Letters, 2024, 35(11): 109893-. doi: 10.1016/j.cclet.2024.109893
16. [16]
  Yi Zhang , Biao Wang , Chao Hu , Muhammad Humayun , Yaping Huang , Yulin Cao , Mosaad Negem , Yigang Ding , Chundong Wang . Fe–Ni–F electrocatalyst for enhancing reaction kinetics of water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100243-100243. doi: 10.1016/j.cjsc.2024.100243
17. [17]
  Yang Yang , Jing-Li Luo , Xian-Zhu Fu . Water-oxidation intermediates enabling electrochemical propylene epoxidation. Chinese Journal of Structural Chemistry, 2024, 43(5): 100269-100269. doi: 10.1016/j.cjsc.2024.100269
18. [18]
  Gu Gong , Mengzhu Li , Ning Sun , Ting Zhi , Yuhao He , Junan Pan , Yuntao Cai , Longlu Wang . Versatile oxidized variants derived from TMDs by various oxidation strategies and their applications. Chinese Chemical Letters, 2024, 35(6): 108705-. doi: 10.1016/j.cclet.2023.108705
19. [19]
  Erzhuo Cheng , Yunyi Li , Wei Yuan , Wei Gong , Yanjun Cai , Yuan Gu , Yong Jiang , Yu Chen , Jingxi Zhang , Guangquan Mo , Bin Yang . Galvanostatic method assembled ZIFs nanostructure as novel nanozyme for the glucose oxidation and biosensing. Chinese Chemical Letters, 2024, 35(9): 109386-. doi: 10.1016/j.cclet.2023.109386
20. [20]
  Zhipeng Wan , Hao Xu , Peng Wu . Selective oxidation using in-situ generated hydrogen peroxide over titanosilicates. Chinese Journal of Structural Chemistry, 2024, 43(6): 100298-100298. doi: 10.1016/j.cjsc.2024.100298

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(574)
HTML views(7)

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

Direct oxidative C(sp3) -H cyanation of secondary benzylic ethers

Metrics

通讯作者: 陈斌, bchen63@163.com

Direct oxidative C(sp³) -H cyanation of secondary benzylic ethers