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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 7: 2201 - 2213

DOI: https://doi.org/10.6023/cjoc202202012

ARTICLES

Synthesis of Dihydrobenzooxaphospholes via Cyclocondensation of 2-Phosphinylphenol and Aldehydes

  • Xueli Zhu ,
  • Shaoli Yang ,
  • Caixia Jia ,
  • Jing Li ,
  • Zheng Duan
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  • aCollege of Chemistry, Green Catalysis Center, International Phosphorus Laboratory, International Joint Research Laboratory for Functional Organophosphorus Materials of Henan Province, Zhengzhou University, Zhengzhou 450001
    bSchool of Chemistry, Xi'an Jiaotong University, Xi'an 710049
* E-mail: ;

Received date: 2022-02-10

  Revised date: 2022-03-16

  Online published: 2022-03-30

Supported by

National Natural Science Foundation of China(22171245); National Natural Science Foundation of China(21672193)

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Abstract

A facile method to synthesize dihydrobenzooxaphospholes was developed from a p-toluenesulfonic acid (p-TSA)- promoted intermolecular cyclocondensation of the readily available 2-phosphinylphenol and aromatic aldehydes. The desired products were obtained as a mixture of stereoisomers. Interestingly, the diastereoisomers could be separated easily by flash column chromatography. The gram-scale and diastereoselective syntheses were also successfully performed.

Key words： organophosphorus; dihydrobenzooxaphosphole; cyclocondensation; diastereoselectivity

Cite this article

Xueli Zhu , Shaoli Yang , Caixia Jia , Jing Li , Zheng Duan . Synthesis of Dihydrobenzooxaphospholes via Cyclocondensation of 2-Phosphinylphenol and Aldehydes[J]. Chinese Journal of Organic Chemistry, 2022 , 42(7) : 2201 -2213 . DOI: 10.6023/cjoc202202012

References

[1]
Tang, W.; Qu, B.; Capacci, A. G.; Rodriguez, S.; Wei, X.; Haddad, N.; Narayanan, B.; Ma, S.; Grinberg, N.; Yee, N. K.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2010, 12, 176.
[2]
(a) Qu, B.; Samankumara, L. P.; Ma, S.; Fandrick, K. R.; Desrosiers, J.-N.; Rodriguez, S.; Li, Z.; Haddad, N.; Han, Z. S.; McKellop, K.; Pennino, S.; Grinberg, N.; Gonnella, N. C.; Song, J. J.; Senanayake, C. H. Angew. Chem., Int. Ed. 2014, 53, 14428.
[2]
(b) Rodriguez, S.; Qu, B.; Fandrick, K. R.; Buono, F.; Haddad, N.; Xu, Y.; Herbage, M. A.; Zeng, X.; Ma, S.; Grinberg, N.; Lee, H.; Han, Z. S.; Yee, N. K.; Senanayake, C. H. Adv. Synth. Catal. 2014, 356, 301.
[2]
(c) Qu, B.; Mangunuru, H. P. R.; Wei, X.; Fandrick, K. R.; Desrosiers, J.-N.; Sieber, J. D.; Kurouski, D.; Haddad, N.; Samankumara, L. P.; Lee, H.; Savoie, J.; Ma, S.; Grinberg, N.; Sarvestani, M.; Yee, N. K.; Song, J. J.; Senanayake, C. H. Org. Lett. 2016, 18, 4920.
[2]
(d) Handa, S.; Andersson, M. P.; Gallou, F.; Reilly, J.; Lipshutz, B. Angew. Chem., Int. Ed. 2016, 55, 4914.
[2]
(e) Qu, B.; Haddad, N.; Rodriguez, S.; Sieber, J. D.; Desrosiers, J.-N.; Patel, N. D.; Zhang, Y.; Grinberg, N.; Lee, H.; Ma, S.; Ries, U. J.; Yee, N. K.; Senanayake, C. H. J. Org. Chem. 2016, 81, 745.
[2]
(f) Wei, X.; Qu, B.; Zeng, X.; Savoie, J.; Fandrick, K. R.; Desrosiers, J.-N.; Tcyrulnikov, S.; Marsini, M. A.; Buono, F.; Li, Z.; Yang, B.-S.; Tang, W.; Haddad, N.; Gutierrez, O.; Wang, J.; Lee, H.; Ma, S.; Campbell, S.; Lorenz, J. C.; Eckhardt, M.; Himmelsbach, F.; Peters, S.; Patel, N. D.; Tan, Z.; Yee, N. K.; Song, J. J.; Roschangar, F.; Kozlowski, M. C.; Senanayake, C. H. J. Am. Chem. Soc. 2016, 138, 15473.
[2]
(g) Haddad, N.; Mangunuru, H. P. R.; Fandrick, K. R.; Qu, B.; Sieber, J. D.; Rodriguez, S.; Desrosiers, J.-N.; Patel, N. D.; Lee, H.; Kurouski, D.; Grinberg, N.; Yee, N. K.; Song, J. J.; Senanayake, C. H. Adv. Synth. Catal. 2016, 358, 3522.
[2]
(h) Li, G.; Wang, X.-J.; Zhang, Y.; Tan, Z.; Decroos, P.; Lorenz, J. C.; Wei, X.; Grinberg, N.; Yee, N. K.; Senanayake, C. H. J. Org. Chem. 2017, 82, 5456.
[2]
(i) Patel, N. D.; Sieber, J. D.; Tcyrulnikov, S.; Simmons, B. J.; Rivalti, D.; Duvvuri, K.; Zhang, Y.; Gao, D. A.; Fandrick, K. R.; Haddad, N.; Lao, K. S.; Mangunuru, H. P. R.; Biswas, S.; Qu, B.; Grinberg, N.; Pennino, S.; Lee, H.; Song, J. J.; Gupton, B. F.; Garg, N. K.; Kozlowski, M. C.; Senanayake, C. H. ACS Catal. 2018, 8, 10190.
[2]
(j) Zatolochnaya, O. V.; Rodriguez, S.; Zhang, Y.; Lao, K. S.; Tcyrulnikov, S.; Li, G.; Wang, X.-J.; Qu, B.; Biswas, S.; Mangunuru, H. P. R.; Rivalti, D.; Sieber, J. D.; Desrosiers, J.-N.; Leung, J. C.; Grinberg, N.; Lee, H.; Haddad, N.; Yee, N. K.; Song, J. J.; Kozlowski, M. C.; Senanayake, C. H. Chem. Sci. 2018, 9, 4505.
[2]
(k) Lu, Z.; Jasinski, J. B.; Handa, S.; Hammond, G. B. Org. Biomol. Chem. 2018, 16, 2748.
[2]
(l) Li, G.; Zatolochnaya, O. V.; Wang, X.-J.; Rodriguez, S.; Qu, B.; Desrosiers, J.-N.; Mangunuru, H. P. R.; Biswas, S.; Rivalti, D.; Karyakarte, S. D.; Sieber, J. D.; Grinberg, N.; Wu, L.; Lee, H.; Haddad, N.; Fandrick, D. R.; Yee, N. K.; Song, J. J.; Senanayake, C. H. Org. Lett. 2018, 20, 1725.
[2]
(m) Xu, G.; Senanayake, C. H.; Tang, W. Acc. Chem. Res. 2019, 52, 1101.
[3]
Zhu, J.; Huang, L.; Dong, W.; Li, N.; Yu, X.; Deng, W.-P.; Tang, W. Angew. Chem., Int. Ed. 2019, 58, 16119.
[4]
Li, C.; Wan, F.; Chen, Y.; Peng, H.; Tang, W.; Yu, S.; McWilliams, J. C.; Mustakis, J.; Samp, L.; Maguire, R. J. Angew. Chem., Int. Ed. 2019, 58, 13573.
[5]
Dong, W.; Xu, X.; Ma, H.; Lei, Y.; Lin, Z.; Zhao, W. J. Am. Chem. Soc. 2021, 143, 10902.
[6]
Qian, C.; Tang, W. Org. Lett. 2020, 22, 4483.
[7]
Xiong, W.; Xu, G.; Yu, X.; Tang, W. Organometallics 2019, 38, 4003.
[8]
(a) Takale, B. S.; Thakore, R. R.; Handa, S.; Gallou, F.; Reilly, J.; Lipshutz, B. H. Chem. Sci. 2019, 10, 8825.
[8]
(b) Sieber, J. D.; Buono, F.; Brusoe, A.; Desrosiers, J. N.; Haddad, N.; Lorenz, J. C.; Xu, Y.; Wu, H.; Zhang, L.; Han, Z. S. Roschangar, F.; Song, J. J.; Yee, N. K.; Senanayake, C. H. J. Org. Chem. 2019, 84, 4926.
[9]
Yang, H.; Sun, J.; Gu, W.; Tang, W. J. Am. Chem. Soc. 2020, 142, 8036.
[10]
Li, B.; Li, T.; Aliyu, M.; Li, Z. H.; Tang, W. Angew. Chem., Int. Ed. 2019, 58, 11355.
[11]
Wu, T.; Kang, X.; Bai, H.; Xiong, W.; Xu, G.; Tang, W. Org. Lett. 2020, 22, 4602.
[12]
Heinicke, J.; Tzschach, A. Phosphorus Sulfur Relat. Elem. 1985, 25, 345.
[13]
(a) Li, S.; Han, Z. S.; Viereck, P.; Lee, H.; Kurouski, D.; Senanayake, C. H.; Tsantrizos, Y. S. Org. Lett. 2017, 19, 894.
[13]
(b) Han, Z.S.; Wu, H.; Xu, Y.; Zhang, Y.; Qu, B.; Li, Z.; Caldwell, D. R.; Fandrick, K. R.; Zhang, L.; Roschangar, F.; Song, J.; Senanayake, C. H. Org. Lett. 2017, 19, 1796.
[14]
(a) Heinicke, J.; Tzschach, A. Z. Chem 1980, 20, 342.
[14]
(b) Washington, M. P.; Gudimetla, V. B.; Laughlin, F. L.; Deligonul, N.; He, S.; Payton, J. L.; Simpson, M. C.; Protasiewicz, J. D. J. Am. Chem. Soc. 2010, 132, 4566.
[14]
(c) Washington, M. P.; Payton, J. L.; Simpson, M. C.; Protasiewicz, J. D. Organometallics 2011, 30, 1975.
[14]
(d) Laughlin, F. Li; Deligonul, N.; Rheingold, A. L.; Golen, J. A.; Laughlin, B. J.; Smith, R. C.; Protasiewicz, J. D. Organometallics 2013, 32, 7116.
[14]
(e) Wu, S. S.; Rheingold, A. L.; Protasiewicz, J. D. Chem. Commun. 2014, 50, 11036.
[14]
(f) Laughlin, F. L.; Rheingold, A. L.; Deligonul, N.; Laughlin, B. J.; Smith, R. C.; Higham, L. J.; Protasiewicz, J. D. Dalton Trans. 2012, 41, 12016.
[14]
(g) Wu, S. S.; Deligonal, N.; Protasiewicz, J. D. Dalton Trans. 2013, 42, 14866.
[15]
Oehme, H.; Leissring, E. Tetrahedron 1981, 37, 753.
[16]
Huang, H.; Denne, J.; Yang, C.-H.; Wang, H.; Kang, J. Y. Angew. Chem., Int. Ed. 2018, 57, 6624.
[17]
(a) Melvin, L. S. Tetrahedron Lett. 1981, 22, 3375.
[17]
(b) Heinicke, J.; Böhle, I.; Tzschach, A. J. Organomet. Chem. 1986, 317, 11.
[17]
(c) Dhawan, B.; Redmore, D. J. Org. Chem. 1991, 56, 833.
[17]
(d) Li, S. S.; Wang, G. Q. Phosphorus Sulfur Relat. Elem. 1991, 61, 119.
[17]
(e) Paladino, J.; Guyard, C.; Thurieau, C.; Fauchère, J. - L. Helv. Chim. Acta 1993, 76, 2465.
[17]
(f) Taylor, C. M.; Watson, A. J. Curr. Org. Chem. 2004, 8, 623.
[17]
(g) Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206.
[17]
(h) Jayasundera, K. P.; Watson, A. J.; Taylor, C. M. Tetrahedron Lett. 2005, 46, 4311.
[17]
(i) Yilmaz, E.; Bier, D.; Guillory, X.; Briels, J.; Ruiz-Blanco, Y. B.; Sanchez-Garcia, E.; Ottmann, C.; Kaiser, M. Chem.-Eur. J. 2018, 24, 13807.
[17]
(j) Korb, M.; Lang, H. Chem. Soc. Rev. 2019, 48, 2829.
[17]
(k) Patel, J. J.; Blackburn, T.; Alessi, M.; Sawinski, H.; Snieckus, V. Org. Lett. 2020, 22, 3860.
[18]
(a) Kenny, N. P.; Rajendran, K. V.; Gilheany, D. G. Chem. Commun. 2015, 51, 16561.
[18]
(b) Huang, H.; Denne, J.; Yang, C. H.; Wang, H.; Kang, J. Y. Angew. Chem., Int. Ed. 2018, 57, 6624.
[18]
(c) Melvin, L. S. Tetrahedron Lett. 1981, 22, 3375.
[18]
(d) Yang, S. X.; Li, Y. G.; Wang, J. Chin. J. Org. Chem. 1984, 4, 271. (in Chinese)
[18]
( 杨石先, 李玉桂, 王坚, 有机化学, 1984, 4, 271.)
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