REVIEWS

Progress in the Syntheses of α-Boryl Carbonyl Compounds

  • Zhihao Chen ,
  • Qi Fan ,
  • Biaolin Yin ,
  • Qingjiang Li ,
  • Honggen Wang
Expand
  • a Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510006
    b Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640
* Corresponding author. E-mail:

Received date: 2023-03-17

  Revised date: 2023-04-14

  Online published: 2023-04-26

Supported by

National Natural Science Foundation of China(22022114); National Natural Science Foundation of China(21971261); Guangdong Basic and Applied Basic Research Foun- dation(2020A1515010624); Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program(2017BT01Y093)

Abstract

α-Boryl carbonyl compounds have traditionally been considered thermodynamically unstable and prone to undergo 1,3-boron migration. In recent years, with the development and understanding of sp3-hybridized boron or tetra-coordinated boron, methods for synthesizing stable and separable α-boryl carbonyl compounds have been actively developed. These methods include the insertion reaction of borane with diazo esters, sulfur ylides and other carbene precursors, the free-radical borylation reaction of α,β-unsaturated carbonyl compounds, and late-stage structural modification reactions of boron-contain- ing compounds. The recent advances in the synthesis of α-boryl carbonyl compounds are reviewed based on different reaction types, and the existing challenges and future research directions are discussed.

Cite this article

Zhihao Chen , Qi Fan , Biaolin Yin , Qingjiang Li , Honggen Wang . Progress in the Syntheses of α-Boryl Carbonyl Compounds[J]. Chinese Journal of Organic Chemistry, 2023 , 43(5) : 1706 -1712 . DOI: 10.6023/cjoc202303025

References

[1]
(a) Matteson, D. S. J. Am. Chem. Soc. 1960, 82(16), 4228.
[1]
(b) Matteson, D. S.; Mah, R. W. H. J. Org. Chem. 1963, 28(9), 2171.
[2]
(a) Product Subclass 29: α-Boryl Carbonyl Compounds. In Category 1, Organometallics, Georg Thieme Verlag K. G., Stuttgart, 2005, Vol. 6.
[2]
(b) Dembitsky, V. M.; Tolstikov, G. A.; Srebnik, M. Eurasian Chem.-Technol. J. 2002, 4, 87.
[3]
Cheng, Q.-Q.; Zhu, S.-F.; Zhang, Y.-Z.; Xie, X.-L.; Zhou, Q.-L. J. Am. Chem. Soc. 2013, 135(38), 14094.
[4]
Drikermann, D.; M??el, R. S.; Al-Jammal, W. K.; Vilotijevic, I. Org. Lett. 2020, 22(3), 1091.
[5]
Li, X.; Curran, D. P. J. Am. Chem. Soc. 2013, 135(32), 12076.
[6]
Chen, D.; Zhang, X.; Qi, W.-Y.; Xu, B.; Xu, M.-H. J. Am. Chem. Soc. 2015, 137(16), 5268.
[7]
(a) Loskutova, N. L.; Shvydkiy, N. V.; Nelyubina, Y. V.; Perekalin, D. S. J. Organomet. Chem. 2018, 867, 86.
[7]
(b) Liu, B.; Xu, M.-H. Chin. J. Chem. 2021, 39(7), 1911.
[7]
(c) Sun, Y.-T.; Rao, X.; Xu, W.; Xu, M.-H. Org. Chem. Front. 2022, 9(13), 3467.
[7]
(d) Wang, T.-Y.; Chen, X.-X.; Zhu, D.-X.; Chung, L. W.; Xu, M.-H. Angew. Chem. Int. Ed. 2022, 61(34), e202207008.
[7]
(e) Zhu, D.-X.; Xia, H.; Liu, J.-G.; Chung, L. W.; Xu, M.-H. J. Am. Chem. Soc. 2021, 143(6), 2608.
[7]
(f) Chen, D.; Zhu, D.-X.; Xu, M.-H. J. Am. Chem. Soc. 2016, 138(5), 1498.
[8]
Allen, T. H.; Kawamoto, T.; Gardner, S.; Geib, S. J.; Curran, D. P. Org. Lett. 2017, 19(13), 3680.
[9]
(a) Kan, S. B. J.; Huang, X.; Gumulya, Y.; Chen, K.; Arnold, F. H. Nature 2017, 552(7683), 132.
[9]
(b) Chen, K.; Huang, X.; Zhang, S.-Q.; Zhou, A. Z.; Kan, S. B. J.; Hong, X.; Arnold, F. H. Synlett 2019, 30(4), 378.
[9]
(c) Huang, X.; Garcia-Borràs, M.; Miao, K.; Kan, S. B. J.; Zutshi, A.; Houk, K. N.; Arnold, F. H. ACS Cent. Sci. 2019, 5(2), 270.
[10]
(a) Li, J.; He, H.; Huang, M.; Chen, Y.; Luo, Y.; Yan, K.; Wang, Q.; Wu, Y. Org. Lett. 2019, 21(22), 9005.
[10]
(b) Zhang, S.-S.; Xie, H.; Shu, B.; Che, T.; Wang, X.-T.; Peng, D.; Yang, F.; Zhang, L. Chem. Commun. 2020, 56(3), 423.
[11]
Yang, J.-M.; Zhao, Y.-T.; Li, Z.-Q.; Gu, X.-S.; Zhu, S.-F.; Zhou, Q.-L. ACS Catal. 2018, 8(8), 7351.
[12]
Ren, S.-C.; Zhang, F.-L.; Xu, A.-Q.; Yang, Y.; Zheng, M.; Zhou, X.; Fu, Y.; Wang, Y.-F. Nat. Commun. 2019, 10(1), 1934.
[13]
Zhang, Y.; Liao, Y.; Liu, P.; Ran, Y.; Liu, X. Org. Biomol. Chem. 2022, 20(17), 3550.
[14]
Li, G.; Huang, G.; Sun, R.; Curran, D. P.; Dai, W. Org. Lett. 2021, 23(11), 4353.
[15]
Dai, W.; Geib, S. J.; Curran, D. P. J. Am. Chem. Soc. 2019, 141(31), 12355.
[16]
Qi, J.; Zhang, F.-L.; Jin, J.-K.; Zhao, Q.; Li, B.; Liu, L.-X.; Wang, Y.-F. Angew. Chem. Int. Ed. 2020, 59(31), 12876.
[17]
Chen, G.; Wang, L.; Liu, X.; Liu, P. Adv. Synth. Catal. 2020, 362(14), 2990.
[18]
Liu, X.; Shen, Y.; Lu, C.; Jian, Y.; Xia, S.; Gao, Z.; Zheng, Y.; An, Y.; Wang, Y. Chem. Commun. 2022, 58(60), 8380.
[19]
Miao, Y.-Q.; Li, X.-Y.; Pan, Q.-J.; Ma, Y.; Kang, J.-X.; Ma, Y.-N.; Liu, Z.; Chen, X. Green Chem. 2022, 24(18), 7113.
[20]
Radcliffe, J. E.; Fasano, V.; Adams, R. W.; You, P.; Ingleson, M. J. Chem. Sci. 2019, 10(5), 1434.
[21]
Li, J.; Ballmer, S. G.; Gillis, E. P.; Fujii, S.; Schmidt, M. J.; Palazzolo, A. M. E.; Lehmann, J. W.; Morehouse, G. F.; Burke, M. D. Science 2015, 347(6227), 1221.
[22]
Li, J.; Burke, M. D. J. Am. Chem. Soc. 2011, 133(35), 13774.
[23]
He, Z.; Yudin, A. K. J. Am. Chem. Soc. 2011, 133(35), 13770.
[24]
Corless, V. B.; Holownia, A.; Foy, H.; Mendoza-Sanchez, R.; Adachi, S.; Dudding, T.; Yudin, A. K. Org. Lett. 2018, 20(17), 5300.
[25]
Lv, W.-X.; Zeng, Y.-F.; Li, Q.; Chen, Y.; Tan, D.-H.; Yang, L.; Wang, H. Angew. Chem. Int. Ed. 2016, 55(34), 10069.
[26]
Ivon, Y. M.; Kuchkovska, Y. O.; Voitenko, Z. V.; Grygorenko, O. O. Eur. J. Org. Chem. 2020, 2020(23), 3367.
[27]
Deloux, L.; Skrzypczak-Jankun, E.; Cheesman, B. V.; Srebnik, M.; Sabat, M. J. Am. Chem. Soc. 1994, 116(22), 10302.
[28]
Albarghouti, G.; Rayyan, S. Org. Prep. Proced. Int. 2020, 52(1), 1.
[29]
Hintermann, L.; Labonne, A. Synthesis 2007, 2007(8), 1121.
[30]
Chen, Z.-H.; Su, X.-X.; Li, Q.; Wu, J.-Q.; Ou, T.-M.; Wang, H. Org. Lett. 2023, 25(7), 1099.
Outlines

/