Organic Letters
Letter
(9) (a) Wen, S.; Wang, J.; Luo, Y.; Yang, H. Tetrahedron 2014, 70,
9314. (b) Mahal, H. S.; Venkataraman, K. J. Chem. Soc. 1934, 1767.
conditions using TEMPO as the oxidant selectively afforded
HCF2S-containing 4H-chromen-4-ones and thiophene-fused
chromones in good yield. The protocol provides a novel
practical approach to introduce HCF2S functionality to organic
compounds using cheap and commercially available reagents.
́
̈
(c) Muller, E.; Kalai, T.; Jeko, J.; Hideg, K. Synthesis 2000, 2000,
̈
1415.
(10) (a) Looker, J. H.; McMechan, J. H.; Mader, J. W. J. Org. Chem.
1978, 43, 2344. (b) Allan, J.; Robinson, R. J. Chem. Soc., Trans. 1924,
125, 2192.
(11) (a) Wu, X.; Neumann, H.; Beller, M. Chem. - Eur. J. 2012, 18,
12595. (b) Shen, C.; Li, W.; Yin, H.; Spannenberg, A.; Skrydstrup, T.;
Wu, X. Adv. Synth. Catal. 2016, 358, 466. (c) Zhu, F.; Wang, Z.; Li,
Y.; Wu, X. Chem. - Eur. J. 2017, 23, 3276.
(12) (a) Awuah, E.; Capretta, A. Org. Lett. 2009, 11, 3210. (b) Miao,
H.; Yang, Z. Org. Lett. 2000, 2, 1765. (c) Yang, Q.; Alper, H. J. Org.
Chem. 2010, 75, 948.
ASSOCIATED CONTENT
* Supporting Information
■
S
The Supporting Information is available free of charge at
Experimental details and spectral characterization (PDF)
Accession Codes
(13) Emami, S.; Ghanbarimasir, Z. Eur. J. Med. Chem. 2015, 93, 539.
(14) (a) Xiong, H.; Pannecoucke, X.; Besset, T. Chem. - Eur. J. 2016,
22, 16734. (b) Ni, C.; Hu, M.; Hu, J. Chem. Rev. 2015, 115, 765.
(15) (a) Wang, F.; Zhang, L.; Zheng, J.; Hu, J. J. Fluorine Chem.
2011, 132, 521. (b) Zafrani, Y.; Sod-Moriah, G.; Segall, Y.
Tetrahedron 2009, 65, 5278. (c) Mehta, V. P.; Greaney, M. F. Org.
Lett. 2013, 15, 5036. (d) Ando, M.; Wada, T.; Sato, N. Org. Lett.
2006, 8, 3805. (e) Li, Z.; Dong, J.; Yuan, Z.; Yang, D.; Weng, Z. Org.
Lett. 2018, 20, 6407. (f) Zhang, W.; Wang, F.; Hu, J. Org. Lett. 2009,
11, 2109. (g) Deng, X.; Lin, J.; Zheng, J.; Xiao, J. Chem. Commun.
2015, 51, 8805. (h) Wu, J.; Gu, Y.; Leng, X.; Shen, Q. Angew. Chem.,
Int. Ed. 2015, 54, 7648. (i) Wang, F.; Huang, W.; Hu, J. Chin. J. Chem.
2011, 29, 2717. (j) Bayarmagnai, B.; Matheis, C.; Jouvin, K.; Goossen,
L. J. Angew. Chem., Int. Ed. 2015, 54, 5753. (k) Li, L.; Wang, F.; Ni,
C.; Hu, J. Angew. Chem., Int. Ed. 2013, 52, 12390.
tallographic data for this paper. These data can be obtained
Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
AUTHOR INFORMATION
Corresponding Authors
■
ORCID
(16) (a) Wu, J.; Liu, Y.; Lu, C.; Shen, Q. Chem. Sci. 2016, 7, 3757.
(b) Wu, J.; Lu, C.; Lu, L.; Shen, Q. Chin. J. Chem. 2018, 36, 1031.
(c) Wu, J.; Gu, Y.; Leng, X.; Shen, Q. Angew. Chem., Int. Ed. 2015, 54,
7648. (d) Zhu, D.; Shao, X.; Hong, X.; Lu, L.; Shen, Q. Angew. Chem.,
Int. Ed. 2016, 55, 15807. (e) Li, J.; Zhu, D.; Lv, L.; Li, C. Chem. Sci.
2018, 9, 5781. (f) Zhu, D.; Gu, Y.; Lu, L.; Shen, Q. J. Am. Chem. Soc.
2015, 137, 10547. (g) Arimori, S.; Matsubara, O.; Takada, M.; Shiro,
M.; Shibata, N. R. R. Soc. Open Sci. 2016, 3, 160102. (h) Yan, Q.;
Jiang, L.; Yi, W.; Liu, Q.; Zhang, W. Adv. Synth. Catal. 2017, 359,
2471. (i) Huang, Z.; Matsubara, O.; Jia, S.; Tokunaga, E.; Shibata, N.
Org. Lett. 2017, 19, 934. (j) Zhao, X.; Wei, A.; Li, T.; Su, Z.; Chen, J.;
Lu, K. Org. Chem. Front. 2017, 4, 232. (k) Ismalaj, E.; Le Bars, D.;
Billard, T. Angew. Chem., Int. Ed. 2016, 55, 4790.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We thank the National Natural Science Foundation (NSF) of
China (21572203 and 21472140) and the NSF of Zhejiang
Province (LZ16B020001) for financial support.
(17) (a) Akama, T.; Shida, Y.; Sugaya, T.; Ishida, H.; Gomi, K.;
Kasai, M. J. Med. Chem. 1996, 39, 3461. (b) Donnelly, J. A.; Farrell, D.
F. J. Org. Chem. 1990, 55, 1757. (c) Alam, S.; Sarkar, Z.; Islam, A.
Proc. - Indian Acad. Sci., Chem. Sci. 2004, 116, 29. (d) Liu, R.; Wang,
X.; Cheng, F.; Li, F.; Xu, K.; Tan, G. Youji Huaxue 2016, 36, 2677.
(e) Liu, R.; Zhang, Y.; Xu, K.; Tan, G. Synth. Commun. 2017, 47, 1.
(f) Du, Z.; Ng, H.; Zhang, K.; Zeng, H.; Wang, J. Org. Biomol. Chem.
2011, 9, 6930.
REFERENCES
■
(1) (a) Khadem, S.; Marles, R. J. Molecules 2012, 17, 191. (b) Xu, J.;
Kjer, J.; Sendker, J.; Wray, V.; Guan, H.; Edrada, R.; Lin, W.; Wu, J.;
Proksch, P. J. Nat. Prod. 2009, 72, 662.
(2) (a) Gaspar, A.; Matos, M. J.; Garrido, J.; Uriarte, E.; Borges, F.
́
Chem. Rev. 2014, 114, 4960. (b) Gaspar, A.; Silva, T.; Yanez, M.;
̃
Vina, D.; Orallo, F.; Ortuso, F.; Uriarte, E.; Alcaro, S.; Borges, F. J.
Med. Chem. 2011, 54, 5165. (c) Reis, J.; Gaspar, A.; Milhazes, N.;
Borges, F. J. Med. Chem. 2017, 60, 7941. (d) Keri, R. S.; Budagumpi,
S.; Pai, R. K.; Balakrishna, R. G. Eur. J. Med. Chem. 2014, 78, 340.
(3) (a) Silva, C. F. M.; Pinto, D. C. G. A.; Silva, A. M. S.
ChemMedChem 2016, 11, 2252. (b) Shaveta; Singh, A.; Kaur, M.;
Sharma, S.; Bhatti, R.; Singh, P. Eur. J. Med. Chem. 2014, 77, 185.
(c) Huo, H.; Gu, Y.; Sun, H.; Zhang, Y.; Liu, W.; Zhu, Z.; Shi, S.;
Song, Y.; Jin, H.; Zhao, Y.; Tu, P.; Li, J. Fitoterapia 2017, 118, 49.
(4) Mohana Kumara, P.; Srimany, A.; Ravikanth, G.; Uma Shaanker,
R.; Pradeep, T. Phytochemistry 2015, 116, 104.
(18) Brahms, D. L. S.; Dailey, W. P. Chem. Rev. 1996, 96, 1585.
(5) Yu, D.; Chen, C.; Brossi, A.; Lee, K. H. J. Med. Chem. 2004, 47,
4072. (b) Yu, D.; Brossi, A.; Kilgore, N.; Wild, C.; Allaway, G.; Lee, K.
H. Bioorg. Med. Chem. Lett. 2003, 13, 1575.
(6) Prakash, O.; Kumar, R.; Parkash, V. Eur. J. Med. Chem. 2008, 43,
435.
(7) Nawrot-Modranka, J. N.; Nawrot, E.; Graczyk, J. Eur. J. Med.
Chem. 2006, 41, 1301. (b) Haveliwala, D. D.; Kamdar, N. R.; Mistry,
P. T.; Patel, S. K. Nucleosides, Nucleotides Nucleic Acids 2014, 33, 80.
(8) (a) Irgashev, R. A.; Sosnovskikh, V. Y.; Kalinovich, N.; Kazakova,
̈
O.; Roschenthaler, G. V. Tetrahedron Lett. 2009, 50, 4903.
D
Org. Lett. XXXX, XXX, XXX−XXX