Citation: Xueguo Zhang, Peigen Wang, Liangwei Zhu, Baohua Chen. Rhodium(III)-catalyzed chemodivergent annulations between phenyloxazoles and diazos via C–H activation[J]. Chinese Chemical Letters, ;2021, 32(2): 695-699. doi: 10.1016/j.cclet.2020.06.011 shu

Rhodium(III)-catalyzed chemodivergent annulations between phenyloxazoles and diazos via C–H activation

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China

chbh@lzu.edu.cn

Received Date: 23 April 2020
Revised Date: 30 May 2020
Accepted Date: 8 June 2020
Available Online: 9 June 2020

Figures(6)

Acid-controlled, chemodivergent and redox-neutral annulations for the synthesis of isocoumarins and isoquinolinones have been realized via Rh(III)-catalyzed C—H activation. Diazo compounds act as a carbene precursor, and coupling occurs in one-pot process, where adipic acid and trimethylacetic acid promote chemodivergent cyclizations.
- Rhodium(III)-catalyzed,
- C—H activation,
- Acid-controlled,
- Isocoumarin,
- One-pot process,
- Ring opening/ring closure
1. [1]
  (a) X. Guo, J. Han, Y. Liu, et al., J. Org. Chem. 82 (2017) 11505-11511;
  (b) N. Lv, Z. Chen, Y. Liu, Z. Liu, Y. Zhang, Adv. Synth. Catal. 361 (2019) 4140-4146;
  (c) S. Zhang, B. Wang, X. Jia, Y. Yuan, Adv. Synth. Catal. 361 (2018) 451-455;
  (d) Q. Wang, Y. Xu, X. Yang, Y. Li, X. Li, Chem. Commun. 53 (2017) 9640-9643;
  (e) L. Kong, X. Han, X. Li, Chem. Commun. 55 (2019) 7339-7342.
2. [2]
  (a) Z. Huang, H.N. Lim, F. Mo, M.C. Young, G. Dong, Chem. Soc. Rev. 44 (2015) 7764-7786;
  (b) Y. Huang, W.J. Pan, Z.X. Wang, Org. Chem. Front. 6 (2019) 2284-2290;
  (c) L. Zhang, J. Chen, J. Chen, et al., Tetrahedron Lett. 60 (2019) 1053-1056.
3. [3]
  (a) P.B. Arockiam, C. Bruneau, P.H. Dixneuf, Chem. Rev. 112 (2012) 5879-5918;
  (b) Y. Qin, L. Zhu, S. Luo, Chem. Rev. 117 (2017) 9433-9520;
  (c) Y. Xu, L. Zhang, M. Liu, et al., Org. Biomol. Chem. 17 (2019) 8706-8710;
  (d) Y. Li, F. Wang, S. Yu, X. Li, Adv. Synth. Catal. 358 (2016) 880-886;
  (e) J.A. Ellman, L. Ackermann, B.F. Shi, J. Org. Chem. 84 (2019) 12701-12704;
  (f) D.Y. Wang, S.H. Guo, G.F. Pan, et al., Org. Lett. 20 (2018) 1794-1797;
  (g) M.N. Zhao, Z.H. Ren, D.S. Yang, Z.H. Guan, Org. Lett. 20 (2018) 1287-1290.
4. [4]
  (a) X.G. Li, M. Sun, K. Liu, Q. Jin, P.N. Liu, Chem. Commun. 51 (2015) 2380-2383;
  (b) G.S. Kumar, N.P. Khot, M. Kapur, Adv. Synth. Catal. 361 (2019) 73-78;
  (c) L. Kong, X. Han, X. Li, Chem. Commun. 55 (2019) 7339-7342;
  (d) M. Wang, L. Kong, Q. Wu, X. Li, Org. Lett. 20 (2018) 4597-4600;
  (e) X. Chen, G. Zheng, G. Song, X. Li, Adv. Synth. Catal. 360 (2018) 2836-2842;
  (f) B. Shen, B. Wan, X. Li, Angew. Chem. 130 (2018) 15760-15764;
  (g) S.Y. Yan, P.X. Ling, B.F. Shi, Adv. Synth. Catal. 359 (2017) 2912-2917.
5. [5]
  W.W. Chan, S.F. Lo, Z. Zhou, W.Y. Yu, J. Am. Chem. Soc. 134 (2012) 13565.
6. [6]
  (a) Z. Shi, D.C. Koester, M. Boultadakis-Arapinis, F. Glorius, J. Am. Chem. Soc. 135 (2013) 12204-12207;
  (b) S.S. Cui, Y. Zhang, D. Wang, Q. Wu, Chem. Sci. (2013) 3912-3916;
  (c) Z. Shi, D.C. Koester, M. Boultadakis-Arapinis, F. Glorius, J. Am. Chem. Soc. 135 (2013) 12204-12207;
  (d) X. Yu, S. Yu, J. Xiao, B. Wan, X. Li, J. Org. Chem. 78 (2013) 5444-5452.
7. [7]
  (a) Y.H. Wang, G. Qiu, H. Zhou, W. Xie, J.B. Liu, Tetrahedron 75 (2019) 3850-3855;
  (b) V. Pirovano, M. Marchetti, J. Carbonaro, et al., Dye. Pigment. 173 (2020) 107917-107930;
  (c) X. Chen, Y. Liu, RSC Adv. 7 (2017) 37839-37843.
8. [8]
  (a) G.D. Xu, Z.Z. Huang, Org. Lett. 19 (2017) 6265-6267;
  (b) M. Zheng, L. Huang, Q. Tong, W. Wu, H. Jiang, Eur. J. Org. Chem. 2016 (2016) 663-667;
  (c) N.A. Danilkina, L.Y. Gurskaya, A.V. Vasilyev, I.A. Balova, Eur. J. Org. Chem. 2016 (2016) 739-747.
9. [9]
  (a) F. Lin, Y. Shen, Y. Zhang, et al., Chem. Eur. J. 24 (2018) 551-555;
  (b) T. Izumi, Y. Nishimoto, K. Kohei, A. Kasahara, J. Heterocycl. Chem. 27 (1990) 1419-1424;
  (c) S.L. Zhang, Z.L. Yu, Org. Biomol. Chem. 14 (2016) 10511-10515.
10. [10]
  (a) C. Hu, G. Hong, Y. He, et al., J. Org. Chem. 83 (2018) 4739-4753;
  (b) S. Koley, T. Chanda, B.J. Ramulu, S. Chowdhury, M.S. Singh, Adv. Synth. Catal. 358 (2016) 1195-1201.
11. [11]
  (a) J.W. Ren, Q.L. Zhao, J.A. Xiao, et al., Chem. Eur. J. 25 (2019) 4673-4677;
  (b) X. Guo, Q. Xing, K. Lei, et al., Adv. Synth. Catal. 359 (2017) 4393-4398;
  (c) L.A. Perego, S. Wagschal, R. Grüber, et al., Adv. Synth. Catal. 361 (2019) 151-159.
12. [12]
  (a) S. Capelli, D. Motta, C. Evangelisti, et al., ChemCatChem11 (2019)3075-3084;
  (b) J.W. Jiang, C.C. Tu, C.H. Chen, Y.C. Lin, ChemCatChem 10 (2018) 5449-5458.
13. [13]
  (a) Z. Yang, L. Jie, Z. Yao, Z. Yang, X. Cui, Adv. Synth. Catal. 361 (2019) 214-218;
  (b) Z. Yang, X. Lin, L. Wang, X. Cui, Org. Chem. Front. 4 (2017) 2179-2183;
  (c) R. Zhu, G. Cheng, C. Jia, L. Xue, X. Cui, J. Org. Chem. 81 (2016) 7539-7544;
  (d) Y. Yu, C. Kuai, R. Chauvin, et al., J. Org. Chem. 82 (2017) 8611-8616;
  (e) J. Yu, S. Wen, D. Ba, et al., Org. Lett. 21 (2019) 6366-6369;
  (f) T. Jeong, S.H. Lee, N.K. Mishra, et al., Adv. Synth. Catal. 359 (2017) 2329-2336.
14. [14]
  (a) G.J. Li, Y.L. Pan, Y.L. Liu, H.F. Xu, J.Z. Chen, Org. Lett. 21 (2019) 1740-1743;
  (b) K. Qiao, X. Yuan, L. Wan, et al., Green Chem. 19 (2017) 5789-5793;
  (c) C.C. Yuan, X.L. Chen, J.Y. Zhang, Y.S. Zhao, Org. Chem. Front. 4 (2017) 1867-1871;
  (d) L. Wan, K. Qiao, X. Yuan, et al., Adv. Synth. Catal. 359 (2017) 2596-2604.
15. [15]
  (a) Y. Liu, J. Wu, B. Qian, Y. Shang, Org. Biomol. Chem. 17 (2019) 8768-8777;
  (b) M. Gao, Y. Yang, H. Chen, B. Zhou, Adv. Synth. Catal. 360 (2018) 100-105;
  (c) S. Dhole, W.J. Chiu, C.M. Sun, Adv. Synth. Catal. 361 (2019) 2916-2925;
  (d) Y.N. Aher, D.M. Lade, A.B. Pawar, Chem. Commun. 54 (2018) 6288-6291;
  (e) M.N. Rashed, S. Siddiki, A.S. Touchy, et al., Chem. Eur. J. 25 (2019) 10594-10605;
  (f) X. Chen, S. Hu, R. Chen, et al., RSC Adv. 8 (2018) 4571-4576.
1. [1]
  Ying-Di Hao , Zhi-Qian Lin , Xiao-Yu Guo , Jiao Liang , Can-Kun Luo , Qian-Tao Wang , Li Guo , Yong Wu . Rhodium-catalyzed Doyle-Kirmse rearrangement reactions of sulfoxoniun ylides. Chinese Chemical Letters, 2024, 35(4): 108834-. doi: 10.1016/j.cclet.2023.108834
2. [2]
  Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
3. [3]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
4. [4]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
5. [5]
  Yujia Shi , Yan Qiao , Pengfei Xie , Miaomiao Tian , Xingwei Li , Junbiao Chang , Bingxian Liu . Rhodium-catalyzed enantioselective in situ C(sp³)−H heteroarylation by a desymmetrization approach. Chinese Chemical Letters, 2024, 35(10): 109544-. doi: 10.1016/j.cclet.2024.109544
6. [6]
  Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
7. [7]
  Qiuyun Li , Yannan Zhu , Yining Wang , Gang Qi , Wen-Juan Hao , Kelu Yan , Bo Jiang . Catalytic CH activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones. Chinese Chemical Letters, 2024, 35(9): 109494-. doi: 10.1016/j.cclet.2024.109494
8. [8]
  Jing-Qi Tao , Shuai Liu , Tian-Yu Zhang , Hong Xin , Xu Yang , Xin-Hua Duan , Li-Na Guo . Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade. Chinese Chemical Letters, 2024, 35(6): 109263-. doi: 10.1016/j.cclet.2023.109263
9. [9]
  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
10. [10]
  Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
11. [11]
  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
12. [12]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
13. [13]
  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
14. [14]
  Peng Wang , Jianjun Wang , Ni Song , Xin Zhou , Ming Li . Radical dehydroxymethylative fluorination of aliphatic primary alcohols and diverse functionalization of α-fluoroimides via BF₃·OEt₂-catalyzed C‒F bond activation. Chinese Chemical Letters, 2025, 36(1): 109748-. doi: 10.1016/j.cclet.2024.109748
15. [15]
  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
16. [16]
  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
17. [17]
  Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
18. [18]
  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
19. [19]
  Ming Huang , Xiuju Cai , Yan Liu , Zhuofeng Ke . Base-controlled NHC-Ru-catalyzed transfer hydrogenation and α-methylation/transfer hydrogenation of ketones using methanol. Chinese Chemical Letters, 2024, 35(7): 109323-. doi: 10.1016/j.cclet.2023.109323
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(1210)
HTML views(174)

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