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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 12: 4738 - 4748

DOI: https://doi.org/10.6023/cjoc202110010

ARTICLES

Visible-Light-Induced Regioselective ortho-C—H Phosphonylation of β-Naphthols with Diarylphosphine Oxides

  • Jinwei Yuan ,
  • Yan Liu ,
  • Yuanyuan Ge ,
  • Shaoxuan Dong ,
  • Saiyi Song ,
  • Liangru Yang ,
  • Yongmei Xiao ,
  • Shouren Zhang ,
  • Lingbo Qu
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  • a School of Chemistry & Chemical Engineering, Henan University of Technology, Zhengzhou 450001
    b Institute of Nanostructured Functional Materials, Huanghe Science and Technology College, Zhengzhou 450006
    c College of Chemistry, Zhengzhou University, Zhengzhou 450001
* Corresponding authors. E-mail: ;
;
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Received date: 2021-10-09

  Revised date: 2021-11-09

  Online published: 2021-11-17

Supported by

Natural Science Foundation in Department of Education of Henan Province(21A150016); Innovative Funds Plan of Henan University of Technology(2020ZKCJ29); Fundamental Research Funds for the Henan Provincial Colleges and Universities in Henan University of Technology(2017RCJH08); National Undergraduate Innovation and Entrepreneurship Training Program from the University in Henan Province(201910463009); National Undergraduate Innovation and Entrepreneurship Training Program from the University in Henan Province(201910463013)

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Abstract

A metal-free visible-light-induced regioselective ortho-C—H phosphonylation of β-naphthols with diarylphosphine oxides has been developed using fluorescein as an organophotoredox catalyst in the presence of K2S2O8 at room temperature under N2 atmosphere. This feature along with mild reaction conditions, sensitive functional group tolerance, good to excellent yields, high regioselectivity, and scale-up synthesis makes it an ideal and practical alternative modification of β-naphthols. The experimental result suggests that a radical pathway is involved in the reaction.

Key words： β-naphthols; diarylphosphine oxide; visible-light catalysis; phosphonylation; radical reaction

Cite this article

Jinwei Yuan , Yan Liu , Yuanyuan Ge , Shaoxuan Dong , Saiyi Song , Liangru Yang , Yongmei Xiao , Shouren Zhang , Lingbo Qu . Visible-Light-Induced Regioselective ortho-C—H Phosphonylation of β-Naphthols with Diarylphosphine Oxides[J]. Chinese Journal of Organic Chemistry, 2021 , 41(12) : 4738 -4748 . DOI: 10.6023/cjoc202110010

References

[1]
(a) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
[1]
(b) Vasilev, N.; Elfahmi, R. B.; Kayser, O.; Momekov, G.; Konstantinov, S.; Ionkova, I. J. Nat. Prod. 2006, 69, 1014.
[1]
(c) Neugebauer, R. C.; Uchiechowska, U.; Meier, R.; Hruby, H.; Valkov, V.; Verdin, E.; Sippl, W.; Jung, M. J. Med. Chem. 2008, 51, 1203.
[1]
(d) Roche, S. P.; Porco Jr, J. A. Angew. Chem.,Int. Ed. 2011, 50, 4068.
[1]
(e) Ogata, T.; Yoshida, T.; Shimizu, M.; Tanaka, M.; Fukuhara, C.; Ishii, J.; Nishiuchi, A.; Inamoto, K.; Kimachi, T. Tetrahedron 2016, 72, 1423.
[2]
(a) Shen, A. Y.; Tsai, C. T.; Chen, C. L. Eur. J. Med. Chem. 1999, 34, 877.
[2]
(b) Huang, M. H.; Wa, S. N.; Wang, J. P.; Lin, C. H.; Lu, S. I.; Lian, L. F.; Shen, A. Y. Drug Dev. Res. 2003, 60, 261.
[2]
(c) Chopade, H. N.; Meshram, J. S.; Pagadala, R.; Mungole, A. J. Int. J. Chem. Tech. Res. 2010, 2, 1823.
[2]
(d) Das, B.; Reddy, C. R.; Kashanna, J.; Mamidy, S. K.; G. Kumar, C. Med. Chem. Res. 2012, 21, 3321.
[3]
(a) Li, S.; Yang, X.; Wang, Y.; Zhou, H.; Zhang, B.; Huang, G.; Zhang, Y.; Li, Y. Adv. Synth. Catal. 2018, 360, 4452.
[3]
(b) Chang, C. H.; Sathishkumar, N.; Liao, Y. T.; Chen, H. T.; Han, J. L. Adv. Synth. Catal. 2020, 362, 903.
[3]
(c) Zhang, C.; Cheng, Y.; Li, F.; Luan, Y.; Li, P.; Li, W. Adv. Synth. Catal. 2020, 362, 1286.
[3]
(d) Wang, C. J.; Yang, Q. Q.; Wang, M. X.; Shang, Y. H.; Tong, X. Y.; Deng, Y. H.; Shao, Z. Org. Chem. Front. 2020, 7, 609.
[3]
(e) Wu, S.; Dong, J.; Zhou, D.; Wang, W.; Liu, L.; Zhou, Y. J. Org. Chem. 2020, 85, 14307.
[4]
(a) Lee, H.; Yi, C. S. Eur. J. Org. Chem. 2015, 2015, 1899.
[4]
(b) Paul, V.; Sudalai, A.; Daniel, T.; Srinivasan, K. V. Tetrahedron Lett. 1994, 35, 2601.
[5]
(a) Paniak, T. J.; Kozlowski, M. C. Org. Lett. 2020, 22, 1765.
[5]
(b) Jurrat, M.; Maggi, L.; Lewis, W; Ball, L. T. Nat. Chem. 2020, 12, 260.
[6]
(a) Xiao, F.; Chen, S.; Tian, J.; Huang, H.; Liu, Y.; Deng, G. J. Green Chem. 2016, 18, 1538.
[6]
(b) Zhou, K.; Chen, M.; Yao, L.; Wu, J. Org. Chem. Front. 2018, 5, 371.
[7]
(a) Jia, L.; Tang, Q.; Luo, M.; Zeng, X. J. Org. Chem. 2018, 83, 508.
[7]
(b) Barton, D. H. R.; Greneur, S. L.; Motherwell, W. B. Tetrahedron Lett. 1983, 24, 160.
[7]
(c) Tang, Q.; Zhang, C.; Luo, M. J. Am. Chem. Soc. 2008, 130, 5840.
[8]
(a) Silva, L. T.; Azeredo, J. B.; Saba, S.; Rafique, J.; Bortoluzzi, A. J.; Braga, A. L. Eur. J. Org. Chem. 2017, 2017, 4740.
[8]
(b) Lima, D. B.; Santos, P. H. V.; Fiori, P.; Badshah, G.; Luz, E. Q.; Seckler, D.; Rampon, D. S. ChemistrySelect 2019, 4, 13558.
[8]
(c) Ghosh, T.; Mukherjee, N.; Ranu, B. C. ACS Omega 2018, 3, 17540.
[8]
(d) Meirinho, A. G.; Pereira, V. F.; Martins, G. M.; Saba, S.; Rafique, J.; Braga, A. L.; Mendes, S. R. Eur. J. Org. Chem. 2019, 2019, 6465.
[8]
(e) Huang, X.; Chen, Y.; Zhen, S.; Song, L.; Gao, M.; Zhang, P.; Li, H.; Yuan, B.; Yang, G. J. Org. Chem. 2018, 83, 7331.
[8]
(f) Parumala, S. K. R.; Peddinti, R. K. Green Chem. 2015, 17, 4068.
[8]
(g) Xiao, F.; Chen, S.; Tian, J.; Huang, H.; Liu, Y.; Deng, G. J. Green Chem. 2016, 18, 1538.
[8]
(h) Wang, D.; Zhang, R.; Lin, S.; Yan, Z.; Guo, S. RSC Adv. 2015, 5, 10803.
[8]
(i) Xu, Z. B.; Lu, G. P.; Cai, C. Org. Biomol. Chem. 2017, 15, 2804.
[8]
(j) Kang, X.; Yan, R.; Yu, G.; Pang, X.; Liu, X.; Li, X.; Xiang, L.; Huang, G. J. Org. Chem. 2014, 79, 10605.
[8]
(k) Khaef, S.; Rostami, A.; Khakyzadeh, V.; Zolfigol, M. A.; Taherpour, A. A.; Yarie, M. Mol. Catal. 2020, 484, 110772.
[9]
(a) Georage, A.; Veis, A. Chem. Rev. 2008, 108, 4670.
[9]
(b) Zhao, D.; Wang, R. Chem. Soc. Rev. 2012, 41, 2095.
[9]
(c) Fernández-Pérez, H.; Etayo, P.; Panossian, A.; Vidal-Ferran, A. Chem. Rev. 2011, 111, 2119.
[10]
(a) Falk, A.; Göderz, A. L.; Schmalz, H. G. Angew. Chem., Int. Ed. 2013, 52, 1576.
[10]
(b) Robert, T.; Velder, J.; Schmalz, H. G. Angew. Chem., Int. Ed. 2008, 47, 7718.
[10]
(c) Rubio, M.; Suárez, A.; Álvarez, E.; Pizzano, A. Chem. Commun. 2005, 628.
[10]
(d) Kleman, P.; González-Liste, P. J.; García-Garrido, S. E.; Cadierno, V.; Pizzano, A. ACS Catal. 2014, 4, 4398.
[10]
(e) Takahiro, N.; Yuko, M.; Tamio, H. Org. Lett. 2011, 13, 3674.
[10]
(f) Bakewell, C.; Cao, T. P. A.; Long, N.; Le Goff, X. F.; Auffrant, A.; Williams, C. K. J. Am. Chem. Soc. 2012, 134, 20577.
[10]
(g) Liu, J. Y.; Liu, S. R.; Li, B. X.; Li, Y. G.; Li, Y. S. Organometallics 2011, 30, 4052.
[10]
(h) Han, C.; Zhu, L.; Zhao, F.; Zhang, Z.; Wang, J.; Deng, Z.; Xu, H.; Li, J.; Ma, D.; Yan, P. Chem. Commun. 2014, 50, 2670.
[10]
(i) Han, C.; Zhao, F.; Zhang, Z.; Zhu, L.; Xu, H.; Li, J.; Ma, D.; Yan, P. Chem. Mater. 2013, 25, 4966.
[10]
(j) Shen, R.; Zhang, M.; Xiao, J.; Dong, C.; Han, L. B. Green Chem. 2018, 20, 5111.
[11]
(a) Xie, J.; Li, H.; Xue, Q.; Cheng, Y.; Zhu, C. Adv. Synth. Catal. 2012, 354, 1646.
[11]
(b) Vassilion, S.; Weglarz-Tomczak, E.; Berlicki, Ł.; Pawelczak, M.; Nocek, B.; Mulligan, R.; Joachimiak, A.; Mucha, A. J. Med. Chem. 2014, 57, 8140.
[11]
(c) Mucha, A.; Kafarski, P.; Berlicki, Ł. J. Med. Chem. 2011, 54, 595.
[12]
(a) Yorimitsu, H. Beilstein J. Org. Chem. 2013, 9, 1269.
[12]
(b) Demmer, C. S.; Krogsgaard-Larsen, N.; Bunch, L. Chem. Rev. 2011, 111, 7981.
[13]
(a) Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. Tetrahedron Lett. 1980, 21, 359.
[13]
(b) Montchamp, J. L.; Dumond, Y. R. J. Am. Chem. Soc. 2001, 123, 510.
[14]
(a) Shaikh, R. S.; Ghosh, I.; König, B. Chem.-Eur. J. 2017, 23, 12120.
[14]
(b) Xu, K.; Yang, F.; Zhang, G.; Wu, Y. Green Chem. 2013, 15, 1055.
[14]
(c) Zhang, X.; Liu, H.; Hu, X.; Tang, G.; Zhu, J.; Zhao, Y. Org. Lett. 2011, 13, 3478.
[14]
(d) Feng, C. G.; Ye, M.; Xiao, K. J.; Li, S.; Yu, J. Q. J. Am. Chem. Soc. 2013, 135, 932.
[15]
Yang, J.; Chen, T.; Han, L. B. J. Am. Chem. Soc. 2015, 137, 1782.
[16]
Zhao, Y. L.; Wu, G. J.; Han, F. S. Chem. Commun. 2012, 48, 5868.
[17]
Dhawan, B.; Redmore, D. J. Org. Chem. 1991, 56, 833.
[18]
Xiong, B.; Li, M.; Liu, Y.; Zhou, Y.; Zhao, C.; Goto, M.; Yin, S. F.; Han, L. B. Adv. Synth. Catal. 2014, 356, 781.
[19]
(a) Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Commun. 2010, 2, 527.
[19]
(b) Sun, C. L.; Shi, Z. J. Chem. Rev. 2014, 114, 921.
[19]
(c) Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239176.
[19]
(d) Jin, J.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 1565.
[19]
(e) Zoller, J.; Fabry, D. C.; Rueping, M. ACS Catal. 2015, 5, 390.
[19]
(f) Li, X.; Gu, X.; Li, P. ACS Catal. 2014, 4, 1897.
[19]
(g) Xiao, T.; Li, L.; Lin, G.; Mao, Z.; Zhou, L. Org. Lett. 2014, 16, 4232.
[19]
(h) Yang, W.; Yang, S.; Li, P.; Wang, L. Chem. Commun. 2015, 51, 7520.
[19]
(i) Zhong, J. J.; Meng, Q. Y.; Liu, B.; Li, X. B.; Gao, X. W.; Lei, T.; Wu, C. J.; Li, Z. J.; Tung, C. H.; Wu, L. Z. Org. Lett. 2014, 16, 1988.
[19]
(j) Ishii, T.; Kakeno, Y.; Nagao, K.; Ohmiya, H. J. Am. Chem. Soc. 2019, 141, 3854.
[19]
(k) Hell, S. M.; Meyer, C. F.; Misale, A.; Sap, J. B. I.; Christensen, K. E.; Willis, M. C.; Trabanco, A. A.; Gouverneur, V. Angew. Chem.,Int. Ed. 2020, 132, 11717.
[19]
(l) Chen, F.; Shao, Y.; Li, M.; Yang, C.; Su, S. J.; Jiang, H.; Ke, Z.; Zeng, W. Nat. Commun. 2021, 12, 4261.
[20]
(a) Li, C. X.; Tu, D. S.; Yao, R.; Yan, H.; Lu, C. S. Org. Lett. 2016, 18, 4928.
[20]
(b) Wang, C. H.; Li, Y. H.; Yang, S. D. Org. Lett. 2018, 20, 2382.
[20]
(c) Peng, P.; Lu, Q.; Peng, L.; Liu, C.; Wang, G.; Lei, A. Chem. Commun. 2016, 52, 12338.
[21]
Luo, K.; Chen, Y. Z.; Yang, W. C.; Zhu, J.; Wu, L. Org. Lett. 2016, 18, 452.
[22]
Singsardar, M.; Dey, A.; Sarkar, R.; Hajra, A. J. Org. Chem. 2018, 83, 12694.
[23]
(a) Mai, W. P.; Yuan, J. W.; Zhu, J. L.; Li, Q. Q.; Yang, L. R.; Xiao, Y. M.; Mao, P.; Qu, L. B. ChemistrySelect 2019, 4, 11066.
[23]
(b) Yuan, J. W.; Li, Y. Z.; Mai, W. P.; Yang, L. R.; Qu, L. B. Tetrahedron 2016, 72, 3084.
[23]
(c) Yuan, J. W.; Yang, L. R.; Mao, P.; Qu, L. B. RSC Adv. 2016, 6, 87058.
[24]
(a) Shi, Y.; Chen, R.; Guo, K.; Meng, F.; Cao, S.; Gu, C.; Zhu, Y. Tetrahedron Lett. 2018, 59, 2062.
[24]
(b) Luo, K.; Yang, W. C.; Wu, L. Asian J. Org. Chem. 2017, 6, 350.
[24]
(c) Yoo, W. J.; Kobayashi, S. Green Chem. 2013, 15, 1844.
[24]
(d) Quint, V.; Morlet-Savary, F.; Lohier, J. F.; Lalevée, J.; Gaumont, A. C.; Lakhdar, S. J. Am. Chem. Soc. 2016, 138, 7436.
[24]
(e) Liu, D.; Chen, J. Q.; Wang, X. Z.; Xu, P. F. Adv. Synth. Catal. 2017, 359, 2773.
[24]
(f) Li, Z.; Song, H.; Guo, R.; Zuo, M.; Hou, C.; Sun, S.; He, X.; Sun, Z.; Chu, W. Green Chem. 2019, 21, 3602.
[25]
(a) Liu, Y.; Chen, X. L.; Li, X. Y.; Zhu, S. S.; Li, S. J.; Song, Y.; Qu, B. L.; Yu, B. J. Am. Chem. Soc. 2021, 143, 964.
[25]
(b) Xie, P.; Fan, J.; Liu, Y.; Wo, X.; Fu, W.; Loh, T. P. Org. Lett. 2018, 20, 3341.
[25]
(c) Vil', V. A.; Krylov, I. B.; Terent’ev, A. O. Sci. China Chem. 2021, 64, 681.
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