SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 11: 3766 - 3775

DOI: https://doi.org/10.6023/cjoc202205031

ARTICLES

α-Benzoyloxylation of β-Dicarbonyl Compounds Involving Cyclic Trivalent Iodine Reagents

  • Zhupeng Gao ,
  • Kai Xiang ,
  • Xuetao Xu ,
  • Yating Zhang ,
  • Daoyong Zhu
Expand
  • aSchool of Pharmacy, Lanzhou University, Lanzhou 730000
    bBeijing Institute of Aerospace Testing Technology, Beijing 100074
    cSchool of Biotechnology and Health Science, Wuyi University, Jiangmen, Guangdong 529020
*E-mail: ;

Received date: 2022-05-18

  Revised date: 2022-06-30

  Online published: 2022-07-21

Supported by

Department of Education of Guangdong Province(2017KTSCX185); Department of Education of Guangdong Province(2017KSYS010); Department of Education of Guangdong Province(2019KZDXM035); Science and Technology Program of Gansu Province(20JR10RA608)

Fold

Abstract

A one-pot method for the α-benzoyloxylation of β-dicarbonyl compounds using trivalent iodine reagent was developed. The success of this protocol hinges on the the in situ generation of silylenol ether structure followed by electrical property-promoted reductive rearrangement of a umpolung intermediate. This reaction has good atomic economy, which is not only suitable for gram scale preparation and subsequent derivatization applications, but also expands the application range of cyclic trivalent iodine and its derivatives in the field of polarity reversal.

Key words： trivalent iodine reagent; β-dicarbonyl compound; α-benzoyloxylation; umpolung

Cite this article

Zhupeng Gao , Kai Xiang , Xuetao Xu , Yating Zhang , Daoyong Zhu . α-Benzoyloxylation of β-Dicarbonyl Compounds Involving Cyclic Trivalent Iodine Reagents[J]. Chinese Journal of Organic Chemistry, 2022 , 42(11) : 3766 -3775 . DOI: 10.6023/cjoc202205031

References

[1]
Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
[2]
Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299.
[3]
Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328.
[4]
Koposov, A. Y.; Netzel, B. C.; Yusubov, M. S.; Nemykin, V. N.; Nazarenko, A. Y.; Zhdankin, V. V. Eur. J. Org. Chem. 2007, 2007, 4475.
[5]
Yusubov, M. S.; Yusubova, R. Y.; Funk, T. V.; Chi, K.-W.; Zhdankin, V. V. Synthesis 2009, 2009, 2505.
[6]
Miyamoto, K.; Yokota, Y.; Suefuji, T.; Yamaguchi, K.; Ozawa, T.; Ochiai, M. Chem.-Eur. J. 2014, 20, 5447.
[7]
Chen, H.; Wang, L.; Han, J. Org. Lett. 2020, 22, 3581.
[8]
Chen, H.; Han, J.; Wang, L. Angew. Chem., Int. Ed. 2018, 57, 12313.
[9]
Linde, E.; Bulfield, D.; Kervefors, G.; Purkait, N.; Olofsson, B. Chem 2022, 8, 850.
[10]
Greaney, M. F.; Motherwell, W. B. Tetrahedron Lett. 2000, 41, 4463.
[11]
Ochiai, M.; Miyamoto, K. Eur. J. Org. Chem. 2008, 2008, 4229.
[12]
Seebach, D. Angew. Chem., nt. Ed. 1979, 18, 239.
[13]
Baragwanath, L.; Rose, C. A.; Zeitler, K.; Connon, S. J. J. Org. Chem. 2009, 74, 9214.
[14]
Desvergnes, S.; Py, S.; Vallée, Y. J. Org. Chem. 2005, 70, 1459.
[15]
Exner, C. J.; Laclef, S.; Poli, F.; Turks, M.; Vogel, P. J. Org. Chem. 2011, 76, 840.
[16]
Izquierdo, J.; Hutson, G. E.; Cohen, D. T.; Scheidt, K. A. Angew. Chem., nt. Ed. 2012, 51, 11686.
[17]
De Joarder, D.; Jennings, M. P. Eur. J. Org. Chem. 2015, 2015, 3303.
[18]
Canesi, S. Synlett 2019, 30, 647.
[19]
Xi, Y.-K.; Zhang, H.; Li, R.-X.; Kang, S.-Y.; Li, J.; Li, Y. Chem.-Eur. J. 2019, 25, 3005.
[20]
Eisenberger, P.; Gischig, S.; Togni, A. Chem.-Eur. J. 2006, 12, 2579.
[21]
Liu, T.; Shen, Q. Org. Lett. 2011, 13, 2342.
[22]
Wang, F.; Wang, D.; Mu, X.; Chen, P.; Liu, G. J. Am. Chem. Soc. 2014, 136, 10202.
[23]
Ge, J.; Ding, Q.; Wang, X.; Peng, Y. J. Org. Chem. 2020, 85, 7658.
[24]
Brand, J. P.; Charpentier, J.; Waser, J. Angew. Chem., nt. Ed. 2009, 48, 9346.
[25]
Fernández González, D.; Brand, J. P.; Waser, J. Chem.-Eur. J. 2010, 16, 9457.
[26]
Frei, R.; Waser, J. J. Am. Chem. Soc. 2013, 135, 9620.
[27]
Chen, C. C.; Waser, J. Chem. Commun. 2014, 50, 12923.
[28]
Chen, C. C.; Waser, J. Org. Lett. 2015, 17, 736.
[29]
Zhdankin, V. V.; Krasutsky, A. P.; Kuehl, C. J.; Simonsen, A. J.; Woodward, J. K.; Mismash, B.; Bolz, J. T. J. Am. Chem. Soc. 1996, 118, 5192.
[30]
Deng, Q.-H.; Bleith, T.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2013, 135, 5356.
[31]
Zhang, B.; Studer, A. Org. Lett. 2013, 15, 4548.
[32]
Vita, M. V.; Waser, J. Org. Lett. 2013, 15, 3246.
[33]
Vita, M. V.; Caramenti, P.; Waser, J. Org. Lett. 2015, 17, 5832.
[34]
Frei, R.; Courant, T.; Wodrich, M. D.; Waser, J. Chem.-Eur. J. 2015, 21, 2662.
[35]
Le Vaillant, F.; Wodrich, M. D.; Waser, J. Chem. Sci. 2017, 8, 1790.
[36]
Egami, H.; Shimizu, R.; Sodeoka, M. Tetrahedron Lett. 2012, 53, 5503.
[37]
Janson, P. G.; Ghoneim, I.; Ilchenko, N. O.; Szabó, K. J. Org. Lett. 2012, 14, 2882.
[38]
Egami, H.; Kawamura, S.; Miyazaki, A.; Sodeoka, M. Angew. Chem.,Int. Ed. 2013, 52, 7841.
[39]
Hari, D. P.; Waser, J. J. Am. Chem. Soc. 2016, 138, 2190.
[40]
Bertho, S.; Rey-Rodriguez, R.; Colas, C.; Retailleau, P.; Gillaizeau, I. Chem.-Eur. J. 2017, 23, 17674.
[41]
Wu, D.; Cui, S.-S.; Lin, Y.; Li, L.; Yu, W. J. Org. Chem. 2019, 84, 10978.
[42]
Banerjee, S.; Senthilkumar, B.; Patil, N. T. Org. Lett. 2019, 21, 180.
[43]
Amos, S. G. E.; Nicolai, S.; Waser, J. Chem. Sci. 2020, 11, 11274.
[44]
Jia, Z.; Gálvez, E.; Sebastián, R. M.; Pleixats, R.; álvarez-Larena, á.; Martin, E.; Vallribera, A.; Shafir, A. Angew. Chem., nt. Ed. 2014, 53, 11298.
[45]
Wu, Y.; Arenas, I.; Broomfield, L. M.; Martin, E.; Shafir, A. Chem.-Eur. J. 2015, 21, 18779.
[46]
Tian, J.; Luo, F.; Zhang, C.; Huang, X.; Zhang, Y.; Zhang, L.; Kong, L.; Hu, X.; Wang, Z.-X.; Peng, B. Angew. Chem., nt. Ed. 2018, 57, 9078.
[47]
Zhao, W.; Huang, X.; Zhan, Y.; Zhang, Q.; Li, D.; Zhang, Y.; Kong, L.; Peng, B. Angew. Chem., nt. Ed. 2019, 58, 17210.
[48]
Sousa e Silva, F. C.; Van, N. T.; Wengryniuk, S. E. J. Am. Chem. Soc. 2020, 142, 64.
[49]
Tian, J.; Luo, F.; Zhang, Q.; Liang, Y.; Li, D.; Zhan, Y.; Kong, L.; Wang, Z.-X.; Peng, B. J. Am. Chem. Soc. 2020, 142, 6884.
[50]
Bhujanga Rao, C.; Yuan, J.; Zhang, Q.; Zhang, R.; Zhang, N.; Fang, J.; Dong, D. J. Org. Chem. 2018, 83, 2904.
[51]
Yu, J.; Tian, J.; Zhang, C. Adv. Synth. Catal. 2010, 352, 531.
[52]
Liu, W.-B.; Chen, C.; Zhang, Q.; Zhu, Z.-B. Beilstein J. Org. Chem. 2011, 7, 1436.
[53]
Lee, J.; Oya, S.; Snyder, J. K. Tetrahedron Lett. 1991, 32, 5899.
[54]
Wang, D.; Xu, C.; Zhang, L.; Luo, S. Org. Lett. 2015, 17, 576.
[55]
Lloris, M. E.; Gálvez, N.; Marquet, J.; Moreno-Ma?as, M. Tetrahedron 1991, 47, 8031.
[56]
Terent’ev, A. O.; Vil’, V. A.; Nikishin, G. I.; Adam, W. Synlett 2015, 26, 802.
[57]
Terent'ev, A. O.; Vil', V. A.; Gorlov, E. S.; Nikishin, G. I.; Pivnitsky, K. K.; Adam, W. J. Org. Chem. 2016, 81, 810.
[58]
Bityukov, O. V.; Matveeva, O. K.; Vil', V. A.; Kokorekin, V. A.; Nikishin, G. I.; Terent'ev, A. O. J. Org. Chem. 2019, 84, 1448.
[59]
Zhang, C.; Chen, X.-M.; Luo, Y.; Li, J.-L.; Chen, M.; Hai, L.; Wu, Y. ACS Sustainable Chem. Eng. 2018, 6, 13473.
[60]
Dar'in, D.; Kantin, G.; Krasavin, M. Chem. Commun. 2019, 55, 5239.
[61]
Wang, X.; Ding, Y.; Tao, Y.; Wang, Z.; Wang, Z.; Yan, J. Polym. Chem. 2020, 11, 1708.
[62]
Zhu, J.; Germain, A. R.; Porco Jr, J. A. Angew. Chem.,Int. Ed. 2004, 43, 1239.
[63]
Uyanik, M.; Suzuki, D.; Yasui, T.; Ishihara, K. Angew. Chem., nt. Ed. 2011, 50, 5331.
[64]
Reddi, R. N.; Prasad, P. K.; Sudalai, A. Org. Lett. 2014, 16, 5674.
[65]
Mao, J.; Liu, D.; Li, Y.; Zhao, J.; Rong, G.; Yan, H.; Zhang, G. Catal. Commun. 2015, 70, 62.
[66]
Chang, L.-M.; Yuan, G.-Q. Tetrahedron 2016, 72, 7003.
[67]
Li, C.; Jin, T.; Zhang, X.; Li, C.; Jia, X.; Li, J. Org. Lett. 2016, 18, 1916.
[68]
Li, J.; Yang, Z.; Yang, T.; Yi, J.; Zhou, C. New J. Chem. 2018, 42, 1581.
[69]
Mizar, P.; Wirth, T. Angew. Chem.,Int. Ed. 2014, 53, 5993.
[70]
Iinuma, M.; Moriyama, K.; Togo, H. Eur. J. Org. Chem. 2014, 2014, 772.
[71]
Harper, M. J.; Emmett, E. J.; Bower, J. F.; Russell, C. A. J. Am. Chem. Soc. 2017, 139, 12386.
[72]
Revol-Cavalier, J.; Bultel-Poncé, V.; Guy, A.; Durand, T.; Oger, C.; Galano, J.-M. Org. Lett. 2020, 22, 7455.
Options
Outlines

/

〈 〉