Synthesis 2024; 56(17): 2695-2702
DOI: 10.1055/s-0043-1775373
paper

A Practical Electrochemical Approach for Synthesizing Selenyl-Dihydrobenzofurans and Chromane with a Tetrasubstituted Carbon Center

Qisheng Chen
a   Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, P. R. of China
b   School of Chemical Engineering and Materials, Changzhou University, No. 666 Liaohe Road, Changzhou 213032, P. R. of China
,
Kai Xiang
c   Beijing Key Laboratory of Research and Application for Aerospace Green Propellants, Beijing Institute of Aerospace Testing Technology, Beijing 100074, P. R. of China
,
Yiyi Chen
b   School of Chemical Engineering and Materials, Changzhou University, No. 666 Liaohe Road, Changzhou 213032, P. R. of China
,
Xianqiang Kong
a   Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, P. R. of China
b   School of Chemical Engineering and Materials, Changzhou University, No. 666 Liaohe Road, Changzhou 213032, P. R. of China
,
Xiaohui Chen
a   Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, P. R. of China
b   School of Chemical Engineering and Materials, Changzhou University, No. 666 Liaohe Road, Changzhou 213032, P. R. of China
,
Zhong-Yan Cao
d   College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. of China
› Author Affiliations
Financial supports from NSFC (22102012, 22202021, 22272011, 22201062, and 22372015), Natural Science Foundation of Henan Province (222300420111), and the opening funding of Hubei Key Laboratory of Natural Products Research and Development, China Three Gorges University (2022NPRD02) are gratefully acknowledged.


Abstract

A straightforward and efficient electrochemical method for the anodic oxidative selenenylation of 2-(2-arylallyl)phenols and a 2-(3-arylbut-3-en-1-yl)phenol with diselenides under ambient air conditions has been outlined. This method allows for the synthesis of selenyl-dihydrobenzofurans and a chromane featuring a sterically hindered tetrasubstituted carbon center, demonstrated through 25 examples with yields reaching up to 98%. Initial mechanistic investigations suggest the likely participation of pivotal seleniranium cation species in regulating the reactivity.

Supporting Information



Publication History

Received: 02 May 2024

Accepted after revision: 04 June 2024

Article published online:
24 June 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
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  • References

    • 1a Sahu PK, Umme T, Yu J, Nayak A, Kim G, Noh M, Lee J.-Y, Kim D.-D, Jeong LS. J. Med. Chem. 2015; 58: 8734

    • For two excellent reviews, see:
    • 1b Mugesh G, du Mont W.-W, Sies H. Chem. Rev. 2001; 101: 2125
    • 1c Nogueira CW, Zeni G, Rocha JB. T. Chem. Rev. 2004; 104: 6255
  • 2 Cao Q, Luo J, Zhao X. Angew. Chem. Int. Ed. 2019; 58: 1315
    • 3a Mugesh G, Singh HB. Chem. Soc. Rev. 2000; 29: 347
    • 3b Perin G, Lenardão EJ, Jacob RG, Panatieri RB. Chem. Rev. 2009; 109: 1277
    • 3c Mukherjee AJ, Sanjio S, Zade SS, Singh HB, Sunoj RB. Chem. Rev. 2010; 110: 4357
    • 3d Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
    • 3e Yu J.-M, Cai C. Org. Biomol. Chem. 2018; 16: 490
    • 4a Wang X, Zhang Y, Sun K, Meng J, Zhang B. Chin. J. Org. Chem. 2021; 41: 4588
    • 4b Qu P, Jiang Y.-Q, Wang Y.-H, Liu G.-Q. Green Chem. 2023; 25: 7485
    • 4c Heredia AA, Bouchet LM, Castro-Godoy WD, Argüello JE. Tetrahedron 2023; 148: 133667
    • 4d Liu J, Wan J.-P, Liu Y. Org. Chem. Front. 2024; 11: 597
    • 5a Clive DL. J, Chittattu G, Curtis NJ, Kiel WA, Kwong CK. J. Chem. Soc., Chem. Commun. 1977; 725
    • 5b Nicolaou KC, Magolda RL, Sipio WJ, Barnette WE, Lysenko Z, Joullie MM. J. Am. Chem. Soc. 1980; 102: 3784
    • 5c Tiecco M, Testaferri L, Tingoli M, Bartoli D, Balducci R. J. Org. Chem. 1990; 55: 429
    • 5d Okuma K, Seto JI. Phosphorus, Sulfur Silicon Relat. Elem. 2010; 185: 1014
    • 5e Kostić M, Verdía P, Fernández-Stefanuto V, Puchta R, Tojo E. J. Phys. Org. Chem. 2019; 32: 1
    • 5f Zhang QB, Yuan PF, Kai LL, Liu K, Ban YL, Wang XY, Wu LZ, Liu Q. Org. Lett. 2019; 21: 885
    • 5g Zhou X, Jiang J, Zhang M, Wu Q, Zhu K, Shi D, Hou S, Zhao J, Li P. Chem. Commun. 2024; 60: 4330
    • 5h Wang X.-Y, Zhong Y.-F, Mo Z.-Y, Wu S.-H, Xu Y.-L, Tang H.-T, Pan Y.-M. Adv. Synth. Catal. 2021; 363: 208
    • 5i For one example using 2-(but-3-en-1-yl)phenol as substrate, see ref. 5a.
  • 6 Scheide MR, Schneider AR, Jardim GA. M, Martins GM, Durigon DC, Saba S, Rafique J, Braga AL. Org. Biomol. Chem. 2020; 18: 4916

    • For selected reviews, see:
    • 7a Yan M, Kawamata Y, Baran PS. Chem. Rev. 2017; 117: 13230
    • 7b Tang S, Liu Y, Lei A. Chem 2018; 4: 27
    • 7c Xiong P, Xu H.-C. Acc. Chem. Res. 2019; 52: 3339
    • 7d Ackermann L. Acc. Chem. Res. 2020; 53: 84
    • 7e Siu JC, Fu NK, Lin S. Acc. Chem. Res. 2020; 53: 547
    • 7f Yu Y, Guo P, Zhong J.-S, Yuan Y, Ye K.-Y. Org. Chem. Front. 2020; 7: 131
    • 7g Ma C, Fang P, Liu Z, Xu S, Xu K, Cheng X, Lei A, Xu H, Zeng CC, Mei T.-S. Sci. Bull. 2021; 66: 2412
    • 7h Xu C, Lei A.-W, Mei T.-S, Xu H.-C, Xu K, Zeng C.-C. CCS Chem. 2021; 4: 1120
    • 7i Tan Z, Zhang H, Xu K, Zeng C.-C. Sci. Chin. Chem. 2023; 67: 450
    • 7j Zhou H, Tan H.-T, He W.-M. Chin. J. Catal. 2023; 46: 4
    • 7k Tang H.-T, Pan Y.-Z, Pan Y.-M. Green Chem. 2023; 25: 8313
  • 8 For pioneering examples using diselenides in electrosynthesis, see: Torii S, Uneyama K, Ono M. Tetrahedron Lett. 1980; 21: 2741
  • 9 Zhu D, Ye A.-H, Chen Z.-M. Synthesis 2021; 53: 3744
    • 10a Kong X, Wang Y, Chen Y, Chen X, Lin L, Cao Z.-Y. Org. Chem. Front. 2022; 9: 1288
    • 10b Kong X, Chen Y, Chen X, Lu Z, Wang W, Ni S.-F, Cao Z.-Y. Org. Lett. 2022; 24: 2137
    • 10c Kong X, Chen X, Chen Y, Cao Z.-Y. J. Org. Chem. 2022; 87: 7013
    • 10d Chen X, Wang N.-Z, Cheng Y.-M, Kong X, Cao Z.-Y. Synthesis 2023; 55: 2833
    • 10e Kong X, Chen Y, Chen X, Ma C, Chen M, Wang W, Xu Y.-Q, Ni S.-F, Cao Z.-Y. Nat. Commun. 2023; 14: 6933
    • 10f Kong X, Liu Q, Chen Y, Wang W, Chen H.-F, Wang W, Zhang S, Chen X, Cao Z.-Y. Green Chem. 2024; 26: 3435
    • 11a Kong X, Yu K, Chen Q, Xu B. Asian J. Org. Chem. 2020; 9: 1760
    • 11b Yu F, Li C, Wang C, Zhang H, Cao Z.-Y. Org. Lett. 2021; 23: 7156

      For selected oxyselenenylation examples with different oxygen sources, see:
    • 12a Vukićević RD, Radović M, Konstantinović S. Monatsh. Chem. 1998; 129: 1309
    • 12b Kim Y, Jang J, Kim DY. Asian J. Org. Chem. 2021; 10: 3271
    • 12c Jacques R, Pal R, Parker NA, Sear CE, Smith PW, Ribaucourt A, Hodgson DM. Org. Biomol. Chem. 2016; 14: 5875
    • 12d Guan Z, Wang Y, Wang H, Huang Y, Wang S, Tang H, Zhang H, Lei A. Green Chem. 2019; 21: 4976
    • 12e Sun L, Yuan Y, Yao M, Wang H, Wang D, Gao M, Chen Y.-H, Lei A. Org. Lett. 2019; 21: 1297
    • 12f Li H, Lu F, Xu J, Hu J, Alhumade H, Lu L, Lei A. Org. Chem. Front. 2022; 9: 2786
    • 12g Kharma A, Jacob C, Bozzi IA. O, Jardim GA. M, Braga AL, Salomao K, Gatto CC, Silva MF. S, Pessoa C, Stangier M, Ackermann L, da Silva Junior EN. Eur. J. Org. Chem. 2020; 4474
    • 12h Gao W, Li B, Zong L, Yu L, Li X, Li Q, Zhang X, Zhang S, Xu K. Eur. J. Org. Chem. 2021; 2431
    • 12i Pan C, Liu P, Wu A.-G, Li M, Wen L, Guo W. Chin. J. Org. Chem. 2020; 40: 2855
    • 12j Xiong T.-K, Xia Q, Zhou X.-Q, Li S.-H, Cui F.-H, Tang H.-T, Pan Y.-M, Liang Y. Adv. Synth. Catal. 2023; 365: 2183
    • 12k Lu F, Xu J, Li H, Wang K, Ouyang D, Sun L, Huang M, Jiang J, Hu J, Alhumade H, Lu L, Lei A. Green Chem. 2021; 23: 7982
    • 12l Cheng X, Hasimujiang B, Xu Z, Cai H, Chen G, Mo G, Ruan Z. J. Org. Chem. 2021; 86: 16045
    • 12m Lin X, Fang Z, Zeng C, Zhu C, Pang X, Liu C, He W, Duan J, Qin N, Guo K. Chem. Eur. J. 2020; 26: 13738
    • 12n Lin K, Lan J, Zhu T. Adv. Synth. Catal. 2022; 364: 3466