Visible-Light-Induced Difluoroalkylated Cyclization of Novel Functionalized Aromatic Isocyanides

  • Yingke Feng ,
  • He Wang ,
  • Mengxing Cui ,
  • Ran Sun ,
  • Xin Wang ,
  • Yang Chen ,
  • Lei Li
Expand
  • School of Petrochemical Engineering, Liaoning Petrochemical University, Fushun, Liaoning 113001

Received date: 2023-03-01

  Revised date: 2023-04-03

  Online published: 2023-04-10

Supported by

The National Natural Science Foundation of China(21702087); The National Natural Science Foundation of China(21801105); The Liaoning Revitalization Talents Program(XLYC1907010); The Natural Science Foundation of Liaoning Province(2022MS361); The Natural Science Foundation of Liaoning Province(2021BS249); The Research Project Fund of Liaoning Provincial Department of Education(LJKZ0373); The Research Project Fund of Liaoning Provincial Department of Education(LJKZ0375)

Abstract

In this study, a visible-light photoredox-catalyzed difluoroalkylation of newly designed functionalized aromatic isocyanides with commercially available CF2 precursors was reported. A series of CF2-containing indole-1,2-fused diazepanones were constructed in cascade reaction through a sequence of radical addition/cyclization processes under mild conditions. This reaction not only generated a class of polycyclic indole fused seven-membered nitrogen heterocycles but also expanded the reactions of functionalized isocyanides.

Cite this article

Yingke Feng , He Wang , Mengxing Cui , Ran Sun , Xin Wang , Yang Chen , Lei Li . Visible-Light-Induced Difluoroalkylated Cyclization of Novel Functionalized Aromatic Isocyanides[J]. Chinese Journal of Organic Chemistry, 2023 , 43(8) : 2913 -2925 . DOI: 10.6023/cjoc202303004

References

[1]
(a) Shiri, M. Chem. Rev. 2012, 112, 3508.
[1]
(b) Sharma, U. K.; Sharma, N.; Vachhani, D. D.; Eycken, E. V. Chem. Soc. Rev. 2015, 44, 1836.
[1]
(c) Huang, L.; Arndt, M.; Goo?en, K.; Heydt, H.; Goo?en, L. J. Chem. Rev. 2015, 115, 2596.
[1]
(d) Xu, Z.; Wang, Q.; Zhu, J. Chem. Soc. Rev. 2018, 47, 7882.
[1]
(e) Tanifuji, R.; Minami, A.; Oguri, H.; Oikawa, H. Nat. Prod. Rep. 2020, 37, 1098.
[2]
(a) Ho, C. Y. US 4529724A, 1985.
[2]
(b) Ho, C. Y.; Hageman, W. E.; Pe?rsico, F. J. 1986, 29, 1118.
[2]
(c) Schultz, C.; Link, A.; Leost, M.; Zaharevitz, D. W.; Gussio, R.; Sausville, E. A.; Meijer, L.; Kunick, C. J. Med. Chem. 1999, 42, 2909.
[2]
(d) Beke, G.; Eles, J.; Boros, A.; Farkas, S.; Keseru, G. M. WO 2016/166684A1, 2016.
[3]
(a) Ohta, Y.; Chiba, H.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2008, 10, 3535.
[3]
(b) Hua, H.-L.; Zhang, B.-S.; He, Y.-T.; Qiu, Y.-F.; Wu, X.-X.; Xu, P.-F.; Liang, Y.-M. Org. Lett. 2016, 18, 216.
[3]
(c) Thikekar, T. U.; Selvaraju, M.; Sun, C.-M. Org. Lett. 2016, 18, 316.
[3]
(d) Thikekar, T. U.; Sun, C.-M. Adv. Synth. Catal. 2017, 359, 3388.
[3]
(e) Wang, S.; Shen, Y.-B.; Li, L.-F.; Qiu, B.; Yu, L.; Liu, Q.; Xiao, J. Org. Lett. 2019, 21, 8904.
[3]
(f) Dhole, S.; Chiu, W.-J.; Sun, C.-M. Adv. Synth. Catal. 2019, 361, 2916.
[3]
(g) Wang, S.; Wang, S.; Song, S.; Gao, Q.; Wen, C.; Zhang, Z.; Zheng, L.; Xiang, J. J. Org. Chem. 2021, 86, 6458.
[3]
(h) Ma, C.; Wang, Y.; Chen, G.; Li, J.; Jiang, Y.; Zhang, X.; Fan, X. Org. Chem. Front. 2022, 9, 4663.
[3]
(i) Hao, Y.; Zhou, P.; Niu, K.; Song, H.; Liu, Y.; Zhang, J.; Wang, Q. Adv. Synth. Catal. 2022, 364, 281.
[4]
(a) Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
[4]
(b) Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry, University Science Books, Herndon, VA, 2005.
[5]
Ruijter, E.; Scheffelaar, R.; Orru, R. V. A. Angew. Chem., Int. Ed. 2011, 50, 6234.
[6]
Song, B.; Xu, B. Chem. Soc. Rev. 2017, 46, 1103.
[7]
(a) Zhang, B.; Studer, A. Chem. Soc. Rev. 2015, 44, 3505.
[7]
(b) Wang, C.-H.; Li, Y.-H.; Yang, S.-D. Org. Lett. 2018, 20, 2382.
[7]
(c) Liu, Y.; Li, J.-L.; Liu, X.-G.; Wu, J.-Q.; Huang, Z.-S.; Li, Q.; Wang, H. Org. Lett. 2021, 23, 1891.
[7]
(d) Ye, H.-B.; Zhou, X.-Y.; Li, L.; He, X.-K.; Xuan, J. Org. Lett. 2022, 24, 6018.
[7]
(e) Xiao, P.; Rong, J.; Ni, C.; Guo, J.; Li, X.; Chen, D.; Hu, J. Org. Lett. 2016, 18, 5912.
[7]
(f) Rong, J.; Deng, L.; Tan, T.; Ni, C.; Gu, Y.; Hu, J. Angew. Chem., Int. Ed. 2016, 55, 2743.
[8]
(a) Mitamura, T.; Iwata, K.; Ogawa, A. Org. Lett. 2009, 11, 3422.
[8]
(b) Mitamura, T.; Ogawa, A. J. Org. Chem. 2011, 76, 1163.
[9]
(a) Tobisu, M.; Fujihara, H.; Koh, K.; Chatani, N. J. Org. Chem. 2010, 75, 4841.
[9]
(b) Tobisu, M.; Koh, K.; Furukawa, T.; Chatani, N. Angew. Chem. 2012, 124, 11525.
[10]
(a) Zhang, B.; Studer, A. Org. Lett. 2014, 16, 1216.
[10]
(b) Leifert, D.; Studer, A. Angew. Chem., Int. Ed. 2016, 55, 11660.
[10]
(c) Wang, L.; Studer, A. Org. Lett. 2017, 19, 5701.
[11]
(a) Evoniuk, C. J.; Ly, M.; Alabugin, I. V. Chem. Commun. 2015, 51, 12831.
[11]
(b) Evoniuk, C. J.; Gomes, G. D. P.; Ly, M.; White, F. D.; Alabugin, I. V. J. Org. Chem. 2017, 82, 4265.
[11]
(c) Gomes, G. D. P.; Evoniuk, C. J.; Ly, M.; Alabugin, I. V. Org. Biomol. Chem. 2017, 15, 4135.
[12]
(a) Li, D.; Mao, T.; Huang, J.; Zhu, Q. Org. Lett. 2017, 19, 3223.
[12]
(b) Tang, S.; Wang, J.; Xiong, Z., Xie, Z.; Li, D.; Huang, J.; Zhu, Q. Org. Lett. 2017, 19, 5577.
[12]
(c) Teng, F.; Hu, W.; Hu, H.; Luo, S.; Zhu, Q. Adv. Synth. Catal. 2019, 361, 1414.
[13]
(a) Jiang, H.; Cheng, Y.; Wang, R.; Zheng, M.; Zhang, Y.; Yu, S. Angew. Chem. 2013, 125, 13531.
[13]
(b) Jiang, H.; Cheng, Y.; Wang, R.; Zhang, Y.; Yu, S. Chem. Commun. 2014, 50, 6164.
[13]
(c) Tong, K.; Zheng, T.; Zhang, Y.; Yu, S. Adv. Synth. Catal. 2015, 357, 3681.
[14]
(a) Hu, Z.; Yuan, H.; Men, Y.; Liu, Q.; Zhang, J.; Xu, X. Angew. Chem., Int. Ed. 2016, 55, 7077.
[14]
(b) Gao, Y.; Hu, Z.; Dong, J.; Liu, J.; Xu, X. Org. Lett. 2017, 19, 5292.
[14]
(c) Hu, Z.; Dong, J.; Men, Y.; Lin, Z.; Cai, J.; Xu, X. Angew. Chem., Int. Ed. 2017, 56, 1805.
[14]
(d) Cai, J.; Hu, Z.; Li, Y.; Liu, J.; Xu, X. Adv. Synth. Catal. 2018, 360, 3595.
[15]
(a) Xu, P.; Zhu, Y.-M.; Wang, F.; Wang, S.-Y.; Ji, S.-J. Org. Lett. 2019, 21, 683.
[15]
(b) Xu, P.; Zhu, Y.-M.; Liu, X.-Y.; Zhou, X.-Z.; Wang, S.-Y.; Ji, S.-J. Chin. Chem. Lett. 2021, 32, 413.
[15]
(c) Jiang, S.; Cao, W.-B.; Xu, X.-P.; Ji, S.-J. Org. Lett. 2021, 23, 6740.
[16]
(a) Vidyasagar, A.; Shi, J.; Kreitmeier, P.; Reiser, O. Org. Lett. 2018, 20, 6984.
[16]
(b) Yang, W.-C.; Wei, K.; Sun, X.; Zhu, J.; Wu, L. Org. Lett. 2018, 20, 3144.
[16]
(c) Yuan, Y.; Dong, W.; Gao, X.; Xie, X.; Zhang, Z. Org. Lett. 2019, 21, 469.
[16]
(d) Liu, Y.; Li, S.-J.; Chen, X.-L.; Fan, L.-L.; Li, X.-Y.; Zhu, S.-S.; Qu, L.-B.; Yu, B. Adv. Synth. Catal. 2020, 362, 688.
[16]
(e) Mao, S.; Wang, H.; Liu, L.; Wang, X.; Zhou, M.-D.; Li, L. Adv. Synth. Catal. 2020, 362, 2274.
[16]
(f) Liu, Y.; Chen, X.-L.; Li, X.-Y.; Zhu, S.-S.; Li, S.-J.; Song, Y.; Qu, L.-B.; Yu, B. J. Am. Chem. Soc. 2021, 143, 964.
[16]
(g) Liu, L.; Li, L.; Wang, X.; Sun, R.; Zhou, M.-D.; Wang, H. Org. Lett. 2021, 23, 5826.
[16]
(h) Liu, J.; Li, L.; Bu, X.; Yuan, Y.; Wang, X.; Sun, R.; Zhou, M.-D.; Wang, H. Org. Chem. Front. 2022, 9, 2486.
[17]
(a) Hu, W.; Teng, F.; Hu, H.; Luo, S.; Zhu, Q. J. Org. Chem. 2019, 84, 6524.
[17]
(b) Hu, W.; Wang, X.; Peng, Y.; Luo, S.; Zhao, J.; Zhu, Q. Org. Lett. 2022, 24, 3642.
[17]
(c) Wang, J.; Ren, P.; Gu, G.; Jiang, Z.; Xiang, B.; Tang, S.; Jia, A.-Q. J. Org. Chem. 2022, 87, 9663.
[17]
(d) Yuan, S.; Liu, Y.; Ni, M.; Hao, T.; Peng, Y.; Ding, Q. Chem. Commun. 2022, 58, 10985.
[17]
(e) Yuan, S.; Liu, X.; Huang, Z.; Gui, S.; Diao, Y.; Peng, Y.-Y.; Ding, Q. J. Org. Chem. 2022, 87, 16542.
[17]
(f) Liu, X.; Yuan, S.; Liu, Y.; Ni, M.; Xu, J.; Gui, S.; Peng, Y.-Y.; Ding, Q. J. Org. Chem. 2023, 88, 198.
[18]
(a) Chen, B.; Vicic, D. A. Top. Organomet. Chem. 2014, 52, 113.
[18]
(b) Ni, C.; Hu, M.; Hu, J. Chem. Rev. 2015, 115, 765.
[18]
(c) Hu, X.-S.; He, J.-X.; Dong, S.-Z.; Zhao, Q.-H.; Yu, J.-S.; Zhou, J. Nat. Commun. 2020, 11, 5500.
[19]
(a) Romanenko, V. D.; Kukhar, V. P. Chem. Rev. 2006, 106, 3868.
[19]
(b) Meanwell, N. A. J. Med. Chem. 2011, 54, 2529.
[19]
(c) Hu, J.; Zhang, W.; Wang, F. Chem. Commun. 2009, 7465.
[19]
(d) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
[20]
(a) Li, J.-X.; Li, L.; Zhou, M.-D.; Wang, H. Org. Chem. Front. 2018, 5, 1003.
[20]
(b) Liu, C.; Yang, Y.-J.; Dong, J.-Y.; Zhou, M.-D.; Li, L.; Wang, H. J. Org. Chem. 2019, 84, 9937.
[20]
(c) Yuan, Y.-R.; Li, L.; Bu, X.; Wang, X.; Sun, R.; Zhou, M.-D.; Wang, H. Asian J. Org. Chem. 2022, 11, e202200139.
Outlines

/