SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 3: 1005 - 1012

DOI: https://doi.org/10.6023/cjoc202309019

ARTICLES

Chemoselective Electro-oxidation of Allyl Arene to Ester

  • Mengfan Li ,
  • Xu Cheng
Expand
  • School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023
*E-mail:

Received date: 2023-09-19

  Revised date: 2023-11-29

  Online published: 2023-12-08

Supported by

National Natural Science Foundation of China(22071105); National Natural Science Foundation of China(22031008)

Fold

Abstract

An electrochemical C—H and C—C bond esterification reaction with allyl arene as a substrate is reported. This oxidation takes place selectively at the benzyl＋allyl C—H site instead of other benzylic C—H groups. Since the reaction does not require acid/base catalysis for esterification, tertiary alcohol is suitable for the synthesis of the corresponding ester. In addition, side reactions such as transesterification can be avoided with this neutral protocol.

Key words： allyl; benzyl; electrochemistry; esterification

Cite this article

Mengfan Li , Xu Cheng . Chemoselective Electro-oxidation of Allyl Arene to Ester[J]. Chinese Journal of Organic Chemistry, 2024 , 44(3) : 1005 -1012 . DOI: 10.6023/cjoc202309019

References

[1]
(a) Liang Y.-F.; Jiao N. Acc. Chem. Res. 2017, 50, 1640.
[1]
(b) White M. C.; Zhao J. J. Am. Chem. Soc. 2018, 140, 13988.
[1]
(c) Dalton T.; Faber T.; Glorius F. ACS Cent. Sci. 2021, 7, 245.
[2]
(a) Shi S.-H.; Liang Y.; Jiao N. Chem. Rev. 2021, 121, 485.
[2]
(b) Cheng X.; Lei A.; Mei T.-S.; Xu H.-C.; Xu K.; Zeng C. CCS Chem. 2022, 4, 1120.
[2]
(c) Li M.; Cheng X. Isr. J. Chem. 2023, n/a, e202300067.
[2]
(d) Zhang P.; Wang T.; Gong J. CCS Chem. 2023, 5, 1028.
[3]
(a) Tang S.; Liu Y.; Lei A. Chem 2018, 4, 27.
[3]
(b) Meyer T. H.; Finger L. H.; Gandeepan P.; Ackermann L. Trends Chem. 2019, 1, 63.
[3]
(c) Yuan Y.; Lei A. Acc. Chem. Res. 2019, 52, 3309.
[3]
(d) Qiu Y.; Zhu C.; Stangier M.; Struwe J.; Ackermann L. CCS Chem. 2021, 3, 1529.
[4]
(a) Marko J. A.; Durgham A.; Bretz S. L.; Liu W. Chem. Commun. 2019, 55, 937.
[4]
(b) Sun Y.; Li X.; Yang M.; Xu W.; Xie J.; Ding M. Green Chem. 2020, 22, 7543.
[4]
(c) Atkins A. P.; Rowett A. C.; Heard D. M.; Tate J. A.; Lennox A. J. J. Org. Lett. 2022, 24, 5105.
[4]
(d) Hoque M. A.; Twilton J.; Zhu J.; Graaf M. D.; Harper K. C.; Tuca E.; DiLabio G. A.; Stahl S. S. J. Am. Chem. Soc. 2022, 144, 15295.
[4]
(e) Chen T.-S.; Long H.; Gao Y.; Xu H.-C. Angew. Chem., Int. Ed. 2023, e202310138.
[5]
Seidler J.; Strugatchi J.; G?rtner T.; Waldvogel S. R. MRS Energy Sustainability 2021, 7, 42.
[6]
(a) Horn E. J.; Rosen B. R.; Chen Y.; Tang J.; Chen K.; Eastgate M. D.; Baran P. S. Nature 2016, 533, 77.
[6]
(b) Kazerouni A. M.; McKoy Q. A.; Blakey S. B. Chem. Commun. 2020, 56, 13287.
[7]
Yu X.; Zhao Z.; Zhu L.; Tan S.; Fu W.; Wang L.; An Y. Mol. Catal. 2022, 519, 112152.
[8]
(a) Martinez-Erro S.; Sanz-Marco A.; Bermejo Gómez A.; Vázquez-Romero A.; Ahlquist M. S. G.; Martín-Matute B. J. Am. Chem. Soc. 2016, 138, 13408.
[8]
(b) Hayashi R.; Ando K.; Udagawa T.; Sai M. Adv. Synth. Catal. 2023, 365, 826.
[8]
(c) Yayla H. G.; Wang H.; Tarantino K. T.; Orbe H. S.; Knowles R. R. J. Am. Chem. Soc. 2016, 138, 10794.
[9]
(a) Kang J.-C.; Tu Y.-Q.; Dong J.-W.; Chen C.; Zhou J.; Ding T.-M.; Zai J.-T.; Chen Z.-M.; Zhang S.-Y. Org. Lett. 2019, 21, 2536.
[9]
(b) Chen C.; Kang J.-C.; Mao C.; Dong J.-W.; Xie Y.-Y.; Ding T.-M.; Tu Y.-Q.; Chen Z.-M.; Zhang S.-Y. Green Chem. 2019, 21, 4014.
Options
Outlines

/

〈 〉