Indium-Promoted Efficient Synthesis of Se-Aryl-2,2-dimethylbutaneselenoates

doi:10.6023/cjoc202507026

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (2): 523-530.DOI: 10.6023/cjoc202507026 Previous Articles Next Articles

ARTICLES

铟促进的硒代芳基-2,2-二甲基丁硒酸酯的高效合成

杨凯^a^,^†, 单申^a^,^†, 陈伟铭^a, 黄九忠^a, 张毅^a, 吴庆荣^b^,^*(), 吴高荣^a^,^*()

^a 赣南医科大学药学院江西省中药药理重点实验室江西赣州 341000
^b 赣州市第五人民医院药剂科赣州肝病研究所江西赣州 341000

收稿日期:2025-07-19 修回日期:2025-09-23 发布日期:2025-10-29
通讯作者: 吴庆荣, 吴高荣
作者简介:
^† 共同第一作者
基金资助:
江西省职业早期青年科技人才培养专项(20244BCE52224); 江西省自然科学基金(20252BAC200240)

Indium-Promoted Efficient Synthesis of Se-Aryl-2,2-dimethylbutaneselenoates

Kai Yang^a, Shen Shan^a, Weiming Chen^a, Jiuzhong Huang^a, Yi Zhang^a, Qingrong Wu^b^,^*(), Gaorong Wu^a^,^*()

^a Jiangxi Province Key Laboratory of Pharmacology of Traditional Chinese Medicine, School of Pharmacy, Gannan Medical University, Ganzhou, Jiangxi 341000
^b Department of Pharmacy, Ganzhou Liver Institute, Ganzhou Fifth People’s Hospital, Ganzhou, Jiangxi 341000

Received:2025-07-19 Revised:2025-09-23 Published:2025-10-29
Contact: Qingrong Wu, Gaorong Wu
About author:
^† These authors contributed equally to this work.
Supported by:
Early-Career Young Scientists and Technologists Project of Jiangxi Province(20244BCE52224); Jiangxi Provincial Natural Science Foundation(20252BAC200240)

1. .pdf(2593KB)

Abstract

Selenoester compounds exhibit significant biological activity and are widely used in the synthesis of natural products, protein intermediates, and superconducting materials. However, the current methods for constructing selenoesters suffer from drawbacks such as expensive catalysts, multiple reaction steps, low yields, and poor efficiency to sterically hindered acyl chlorides. Here, an efficient indium-promoted method for the synthesis of Se-aryl-2,2-dimethylbutaneselenoates is developed. The strategy features broad substrate scope, mild reaction conditions and simple operation, offering the desired products in moderate to excellent yields. Furthermore, the gram-scale reaction can be conducted smoothly, laying the foundation for subsequent derivatization of such structures.

Key words: organoselenium compounds, indium-promoted, Se-aryl-2,2-dimethylbutaneselenoates

Cite this article

Kai Yang, Shen Shan, Weiming Chen, Jiuzhong Huang, Yi Zhang, Qingrong Wu, Gaorong Wu. Indium-Promoted Efficient Synthesis of Se-Aryl-2,2-dimethylbutaneselenoates[J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 523-530.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 3

References 11

[2]	(h) Xian L.-M.; Li Q.-R.; Li T.; Yu L. Chin. Chem. Lett. 2023, 34, 107878.
	(i) Liu M.-X.; Zhang X.-L.; Chu S.-N.; Ge Y.-Y.; Huang T.; Liu Y.-H.; Yu L. Chin. Chem. Lett. 2022, 33, 205.
	(j) Cao J.-L.; Zhou Y.-H.; Gong X.-R.; Ren M.-L.; Chen Y.-Y.; Xu Y.-L. Adv. Synth. Catal. 2025, 367, e202500098.
	(k) Ren M.-L.; Liang S.-M.; Lin S.-T.; Huang R.-Z.; Chen Y.-Y.; Zhang Y.; Xu Y.-L. Bioorg. Chem. 2024, 152, 107733.
	(l) Gong X.-R.; Sun S.-S.; Ren M.-L.; Wu Q.-Y.; Chen Y.-Y.; Xu Y.-L. J. Org. Chem. 2024, 89, 4176.
[1]	a) Ding W.-Q.; Wang S.; Gu J.-X.; Yu L. Chin. Chem. Lett. 2023, 34, 108043.
	(b) Gu J.-J.; Gu J.-X.; Yu L. Chin. Chem. Lett. 2025, 36, 110727.
[2]	a) Gallo-Rodriguez C.; Rodriguez J. B. ChemMedChem 2024, 19, e202400063.
	(b) Gallo-Rodriguez C.; Rodriguez J. B. Synthesis 2024, 56, 2295.
	(c) Chen S.-S.; Fan C.-Y.; Xu Z.-J.; Pei M.-Y.; Wang J.-M.; Zhang J.-Y.; Zhang Y.-L.; Li J.-Y.; Lu J.-L.; Peng C.; Wei X.-F. Nat. Commun. 2024, 15, 769.
	(d) Cao K.-H.; Chu S.-N.; Ding Y.-H.; Lu S.-M.; Yu L; Du J. Chin. Chem. Lett. 2025, DOI: 10.1016/j.cclet.2025.111486.
	(m) Sun S.-S.; Mo Z.-Y.; Chen Y.-Y.; Xu Y.-L. J. Org. Chem. 2022, 87, 12477.
	(n) Liu H.-Y.; Zhang J.-R.; Huang G.-B.; Zhou Y.-H.; Chen Y.-Y.; Xu Y.-L. Adv. Synth. Catal. 2021, 363, 1656.
	(o) Zhang J.-R.; Liu H.-Y.; Fan T.; Chen Y.-Y.; Xu Y.-L. Adv. Synth. Catal. 2021, 363, 497.
	(p) Ma X.-L.; Wang Q.; Feng X.-Y.; Mo Z.-Y.; Pan Y.-M.; Chen Y.-Y.; Xin M.; Xu Y.-L. Green Chem. 2019, 21, 3547.
	(q) Sun K.; Wang X.; Li C.; Wang H.; Li L. Org. Chem. Front. 2020, 7, 3100.
	(e) Li X.-X.; Zhou H.-W.; Qian R.-R.; Zhang X.; Yu L. Chin. Chem. Lett. 2025, 36, 110036.
	(f) Chen X.-Y.; Zhuang S.-H.; Yan W.-Y.; Zeng Z.-L.; Feng J.-G.; Cao H.-G.; Yu L. Chin. Chem. Lett. 2024, 35, 109635.
	(g) Li J.-H.; Shi Q.; Xue Y.; Zheng M.-D.; Liu L.; Geng T.-Y.; Gong D.-Q.; Zhao M.-M. Chin. Chem. Lett. 2024, 35, 109239.
	(r) Wang X.; Meng P.-P.; Zhao D.-Y.; Tang S.; Sun K. Chin. Chem. Lett. 2023, 34, 107736.
	(s) Wang X.; Wang Z.-C.; Li Z.-J.; Sun K. Chin. Chem. Lett. 2023, 34, 108045.
	(t) Shi T.-T.; Tian M.; Sun Z.-F.; Zou R.X.; Zhang Z.-X.; Xie N.; Hao E.-J.; Xu X.-M.; Sun K. Chem. Commun. 2025, 61, 4066.
	(u) Zhang Z.; Tan P.-P.; Wang S.-L.; Wang H.-Z.; Xie L.; Chen Y.; Han L.-L.; Yang S.-B.; Sun K. Org. Lett. 2023, 25, 4208.
[3]	a) Pandey G.; Tiwari S. K.; Singh B.; Vanka K.; Jain S. Chem. Commun. 2017, 53, 12337.
	(b) Bennasar M. L.; Roca T.; Ferrando F. Org. Lett. 2006, 8, 561.
	(c) Koketsu M.; Miyajima Y.; Ishihara H. Chem. Lett. 1998, 27, 645.
	(d) Takei T.; Andoh T.; Takao T.; Hojo H. Angew. Chem. Int. Ed. 2017, 56, 15708.
	(e) Kulkarni S. S.; Sayers J.; Premdjee B.; Payne R. J. Nat. Chem. Rev. 2018, 2, 0122.
[4]	Baldassari L. L.; Lüdtke D. S. Chem.-Eur. J. 2021, 27, 8656.
[5]	Duarte J. S.; De Oliveira S. A.; Da Silva E. C. O.; De Jesus A. P. V.; Vasconcelos L. G.; De Sousa Júnior P. T.; Rafique J.; Saba S.; Stein A. L. Asian J. Org. Chem. 2023, 12, e202300474.
[6]	Angeli A.; Carta F.; Donnini S.; Capperucci A.; Ferroroni M.; Tanini D.; Supuran C. T. Chem. Commun. 2020, 56, 4444.
[7]	a) Narayanaperumal S.; Alberto E. E.; Gul K.; Kawasoko C. Y.; Dornelles L.; Rodrigues O. E. D.; Braga A. L. Tetrahedron 2011, 67, 4723.
	(b) Godoi M.; Ricardo E. W.; Botteselle G. V.; Galetto F. Z.; Azeredo J. B.; Braga A. L. Green Chem. 2012, 14, 456.
	(c) Silveira C. C.; Braga A. L.; Larghi E. L. Organometallics 1999, 18, 5183.
	(d) Nishiyama Y.; Kawamatsu H.; Funato S.; Tokunaga K.; Sonoda N. J. Org. Chem. 2003, 68, 3599.
	(e) Zhang Y.; Yu Y.; Lin R. Synth. Commun. 1993, 23, 189.
	(f) Chen R.; Zhang Y. Synth. Commun. 2000, 30, 1331.
	(g) Ren K.; Wang M.; Liu P.; Wang L. Synthesis 2010, 1078.
	(h) De Oliveira A. J.; De Oliveira S. A.; Vasconcelos L. G.; Dall'oglio E. L.; Vieira L. C. C.; Stein A. L. Tetrahedron Lett. 2021, 80, 153317.
	(i) Marin G.; Braga A. L.; Rosa A. S.; Galetto F. Z.; Burrow R. A.; Gallardo H.; Paixão M. W. Tetrahedron 2009, 65, 4614.
	(j) Ranu B. C.; Mandal T.; Samanta S. Org. Lett. 2003, 5, 1439.
	(k) Ranu B. C.; Mandal T. J. Org. Chem. 2004, 69, 5793.
[8]	a) Feng J.; Xi L.-L.; Lu C.-J.; Liu R.-R. Chem. Soc. Rev. 2024, 53, 9560.
	(b) Zhao Z.-J.; Zhang F.-R.; Wang D.-Y.; Deng L. Chin. J. Chem. 2023, 41, 3063.
[9]	a) Kumar G.; Bhattacharya D.; Mistry P.; Chatterjee I. J. Org. Chem. 2023, 88, 6987.
	(b) Wu W.; Zhang F.-Q.; Liu N.; Wei Z.-X.; Xu J.-B.; He Z.-X.; Guo Y.-F.; Fan B.-M. Asian. J. Org. Chem. 2022, 11, e202200336.
[10]	a) Wu G.-R.; Xu X.-B.; Wang S.; Chen L.; Pang B.-H.; Ma T.; Ji Y.-F. Chin. Chem. Lett. 2022, 33, 2005.
	(b) Wu G.-R.; Ma T. Chin. Chem. Lett. 2025, DOI: 10.1016/j.cclet.2025.111739.
[11]	Chen Y.-N.; Yang Y.-N.; He X.-N.; Liu X..; Yu P.-C.; Liu R.-R.; Wei L.-Q.; Zhang B.; Zou T.-S.; Liu H.-X.; Li Y.-Q.; Chen R.; Cheng Y. Acta Biomater. 2023, 17, 495.

铟促进的硒代芳基-2,2-二甲基丁硒酸酯的高效合成

Indium-Promoted Efficient Synthesis of Se-Aryl-2,2-dimethylbutaneselenoates

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 3

References 11

Related Articles 1

Recommended Articles

Metrics

Comments