Organic Letters
Letter
Y.; Li, G.; Jiao, H.; Dai, C.; Li, Y.; Zhang, C.; Liu, L. Chem. Commun.
2016, 52, 8471.
In conclusion, we have developed a new and efficient
strategy for the synthesis of cyclohexanone derivatives via
electrochemically oxidative selenylation/1,2-carbon migration
and Dowd−Beckwith-type rearrangement sequences of
alkenylcyclobutanol derivatives 1 with diselenides 2. This
approach is environmentally benign by using shelf-stable
diselenides as selenium radical precursors and electrons as
oxidizing reagents. The present protocol is an efficient option
for synthesizing β-selenated cyclic ketone and one-carbon
expanded cyclic ketone derivatives.
(4) Reviews for reactions with diselenides, see: (a) Beletskaya, I. P.;
Ananikov, V. P. Chem. Rev. 2011, 111, 1596. (b) Ivanova, A.;
Arsenyan, P. Coord. Chem. Rev. 2018, 370, 55. For selected examples
for the reaction of diselenides with various substrates, see: (c) Zheng,
Y.; He, Y.; Rong, G.; Zhang, X.; Weng, Y.; Dong, K.; Xu, X.; Mao, J.
Org. Lett. 2015, 17, 5444. (d) Sun, J.; Zhang-Negrerie, D.; Du, Y. Adv.
Synth. Catal. 2016, 358, 2035. (e) Qiu, J.-K.; Shan, C.; Wang, D.-C.;
Wei, P.; Jiang, B.; Tu, S.-J.; Li, G.; Guo, K. Adv. Synth. Catal. 2017,
359, 4332. (f) Zhu, Y.-Q.; He, J.-L.; Niu, Y.-X.; Kang, H.-Y.; Han, T.-
F.; Li, H.-Y. J. Org. Chem. 2018, 83, 9958. (g) Liu, Y.; Li, C.; Mu, S.;
Li, Y.; Feng, R.; Sun, K. Asian J. Org. Chem. 2018, 7, 720. (h) Yu, J.-
M.; Cai, C. Org. Biomol. Chem. 2018, 16, 490. (i) Zhao, F.; Sun, T.;
Liu, Z.; Sun, K.; Zhang, C.; Wang, X. Curr. Org. Chem. 2018, 22, 613.
(j) Wu, P.; Wu, K.; Wang, L.; Yu, Z. Org. Lett. 2017, 19, 5450.
ASSOCIATED CONTENT
* Supporting Information
■
S
The Supporting Information is available free of charge on the
(k) Ricordi, V. G.; Freitas, C. S.; Perin, G.; Lenardao, E. J.; Jacob, R.
̃
G.; Savegnago, L.; Alves, D. Green Chem. 2012, 14, 1030. (l) Zheng,
B.; Gong, Y.; Xu, H.-J. Tetrahedron 2013, 69, 5342. (m) Kumar, A.;
Kumar, S. Tetrahedron 2014, 70, 1763. (n) Jana, S.; Chakraborty, A.;
Mondal, S.; Hajra, A. RSC Adv. 2015, 5, 77534. (o) Ricordi, V. G.;
Experimental procedures and characterization data
Thurow, S.; Penteado, F.; Schumacher, R. F.; Perin, G.; Lenardao, E.
̃
AUTHOR INFORMATION
J.; Alves, D. Adv. Synth. Catal. 2015, 357, 933. (p) Yu, S.; Wan, B.; Li,
X. Org. Lett. 2015, 17, 58. (q) Ferreira, N. L.; Azeredo, J. B.;
Fiorentin, B. L.; Braga, A. L. Eur. J. Org. Chem. 2015, 2015, 5070.
(r) Mandal, A.; Sahoo, H.; Baidya, M. Org. Lett. 2016, 18, 3202.
(s) Sahoo, H.; Mandal, A.; Selvakumar, J.; Baidya, M. Eur. J. Org.
Chem. 2016, 2016, 4321. (t) Gandeepan, P.; Koeller, J.; Ackermann,
L. ACS Catal. 2017, 7, 1030. (u) Kibriya, G.; Samanta, S.; Singsardar,
M.; Jana, S.; Hajra, A. Eur. J. Org. Chem. 2017, 2017, 3055. (v) Zhang,
Q.-B.; Ban, Y.-L.; Yuan, P.-F.; Peng, S.-J.; Fang, J.-G.; Liu, L.-Z. W. Q.
Green Chem. 2017, 19, 5559. (w) Saba, S.; Rafique, J.; Franco, M. S.;
Schneider, A. R.; Espíndola, L.; Silva, D. O.; Braga, A. L. Org. Biomol.
Chem. 2018, 16, 880. (x) Kumaraswamy, G.; Ramesh, V.; Gangadhar,
M.; Vijaykumar, S. Asian J. Org. Chem. 2018, 7, 1689. (y) Mukherjee,
N.; Chatterjee, T.; Ranu, B. C. J. Org. Chem. 2013, 78, 11110.
(z) Kundu, D.; Ahammed, S.; Ranu, B. C. Org. Lett. 2014, 16, 1814.
(5) Reviews for difunctionalization of alkenes: (a) Chen, Z.-M.;
Zhang, X.-M.; Tu, Y.-Q. Chem. Soc. Rev. 2015, 44, 5220. (b) Courant,
T.; Masson, G. J. Org. Chem. 2016, 81, 6945. (c) Studer, A.; Curran,
D. P. Angew. Chem., Int. Ed. 2016, 55, 58. (d) Tian, Y.; Chen, S.; Gu,
Q.-S.; Lin, J.-S.; Liu, X.-Y. Tetrahedron Lett. 2018, 59, 203. Selected
reports: (e) Chen, Y.; Duan, W.-L. J. Am. Chem. Soc. 2013, 135,
16754. (f) Unoh, Y.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem.,
Int. Ed. 2013, 52, 12975. (g) Gao, P.; Shen, Y.-W.; Fang, R.; Hao, X.-
H.; Qiu, Z.-H.; Yang, F.; Yan, X.-B.; Wang, Q.; Gong, X.-J.; Liu, X.-Y.;
Liang, Y.-M. Angew. Chem., Int. Ed. 2014, 53, 7629. (h) Douglas, J. J.;
Albright, H.; Sevrin, M. J.; Cole, K. P.; Stephenson, C. R. J. Angew.
Chem., Int. Ed. 2015, 54, 14898. (i) Zhou, T.; Luo, F.-X.; Yang, M.-Y.;
Shi, Z.-J. J. Am. Chem. Soc. 2015, 137, 14586. (j) Zhang, Y.-X.; Jin, R.-
X.; Yin, H.; Li, Y.; Wang, X.-S. Org. Lett. 2018, 20, 7283.
(k) Nakafuku, K. M.; Fosu, S. C.; Nagib, D. A. J. Am. Chem. Soc.
2018, 140, 11202.
(6) Review for aryl migration reaction: (a) Zeng, Y.; Ni, C.; Hu, J.
Chem. - Eur. J. 2016, 22, 3210. Selected reports: (b) Thaharn, W.;
Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.;
Pohmakotr, M. Angew. Chem., Int. Ed. 2014, 53, 2212. (c) Li, L.;
Li, Z.-L.; Wang, F.-L.; Guo, Z.; Cheng, Y.-F.; Wang, N.; Dong, X.-W.;
Fang, C.; Liu, J.; Hou, C.; Tan, B.; Liu, X.-Y. Nat. Commun. 2016, 7,
13852. (d) Li, L.; Gu, Q.-S.; Wang, N.; Song, P.; Li, Z.-L.; Li, X.-H.;
Wang, F.-L.; Liu, X.-Y. Chem. Commun. 2017, 53, 4038. (e) Wang, N.;
Gu, Q.-S.; Li, Z.-L.; Guo, Y.-L.; Kiu, X.-Y. Angew. Chem., Int. Ed. 2018,
57, 14225.
(7) (a) Shu, X.-Z.; Zhang, M.; He, Y.; Frei, H.; Toste, F. D. J. Am.
Chem. Soc. 2014, 136, 5844. (b) Sahoo, B.; Li, J.-L.; Glorius, F. Angew.
Chem., Int. Ed. 2015, 54, 11577. (c) Suh, C. W.; Kim, D. Y.
Tetrahedron Lett. 2015, 56, 5661. (d) Woo, S. B.; Kim, D. Y. J.
Fluorine Chem. 2015, 178, 214. (e) Kwon, S. J.; Kim, Y. J.; Kim, D. Y.
Tetrahedron Lett. 2016, 57, 4371. (f) Kwon, S. J.; Kim, D. Y. Org. Lett.
■
Corresponding Author
ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This research was supported by Soonchunhyang University
Research Fund and Basic Science Research Program through
the National Research Foundation of Korea (NRF-
2016R1D1A1B03933723).
REFERENCES
■
(1) (a) Mugesh, G.; Singh, H. B. Acc. Chem. Res. 2002, 35, 226.
(b) Nogueira, C. W.; Zeni, G.; Rocha, J. B. T. Chem. Rev. 2004, 104,
6255. (c) Kumar, S.; Johansson, H.; Kanda, T.; Engman, L.; Muller,
̈
T.; Bergenudd, H.; Jonsson, M.; Pedulli, G. F.; Amorati, R.;
Valgimigli, L. J. Org. Chem. 2010, 75, 716. (d) Sarma, B. K.;
Manna, D.; Minoura, M.; Mugesh, G. J. Am. Chem. Soc. 2010, 132,
5364. (e) Santi, C. In Organoselenium Chemistry Between Synthesis and
Biochemistry; Bentham Books, 2014. (f) Sancineto, L.; Mariotti, A.;
Bagnoli, L.; Marini, F.; Desantis, J.; Iraci, N.; Santi, C.; Pannecouque,
C.; Tabarrini, O. J. Med. Chem. 2015, 58, 9601. (g) Mondal, S.;
Manna, D.; Mugesh, G. Angew. Chem., Int. Ed. 2015, 54, 9298.
(h) Pang, Y.; An, B.; Lou, L.; Zhang, J.; Yan, J.; Huang, L.; Li, X.; Yin,
S. J. Med. Chem. 2017, 60, 7300. (i) Kibriya, G.; Samanta, S.;
Singsardar, M.; Jana, S.; Hajra, A. Eur. J. Org. Chem. 2017, 2017, 3055.
(j) Jain, V. K., Priyadarsini, K. I., Eds. Organoselenium Compounds in
Biology and Medicine; RSC: Cambridge, 2017.
(2) (a) Silveira, C. C.; Braga, A. L.; Vieira, A. S.; Zeni, G. J. Org.
Chem. 2003, 68, 662. (b) Kundu, D.; Ahammed, S.; Ranu, B. C. Org.
Lett. 2014, 16, 1814. (c) Luo, J.; Zhu, Z.; Liu, Y.; Zhao, X. Org. Lett.
2015, 17, 3620. (d) Verma, A.; Jana, S.; Prasad, C. D.; Yadav, A.;
Kumar, S. Chem. Commun. 2016, 52, 4179.
(3) (a) Zeni, G.; Ludtke, D. S.; Panatieri, R. B.; Braga, A. L. Chem.
Rev. 2006, 106, 1032. (b) Perin, G.; Lenardao, E. J.; Jacob, R. G.;
Panatieri, R. B. Chem. Rev. 2009, 109, 1277. (c) Freudendahl, D. M.;
Santoro, S.; Shahzad, S. A.; Santi, C.; Wirth, T. Angew. Chem., Int. Ed.
2009, 48, 8409. (d) Abdo, M.; Zhang, Y.; Schramm, V. L.; Knapp, S.
Org. Lett. 2010, 12, 2982. (e) Rafique, J.; Saba, S.; Rosario, A. R.;
Braga, A. L. Chem. - Eur. J. 2016, 22, 11854. (f) Shu, S.; Fan, Z.; Yao,
Q.; Zhang, A. J. Org. Chem. 2016, 81, 5263. (g) Sun, K.; Wang, X.; Lv,
D
Org. Lett. XXXX, XXX, XXX−XXX