Organic Letters
Letter
the radical intermediate B via a Ag(II)-promoted SET process,
Khandelwal, A.; Upreti, V. V.; Mamidi, S. R. Eur. J. Med. Chem. 2003,
3
(
8, 811.
3) (a) Aziz, J.; Messaoudi, S.; Alami, M.; Hamze, A. Org. Biomol.
would react with H O to form the enolate adduct D. Finally,
2
further isomerization of D led to the formation of the desired
product 3aa.
Chem. 2014, 12, 9743. (b) Emmett, E. J.; Willis, M. C. Asian J. Org.
Chem. 2015, 4, 602.
In summary, we have developed a highly efficient protocol
for the preparation of various sulfonylated benzofurans via a
Ag-catalyzed oxidative cyclization reaction of 1,6-enynes and
sodium sulfinates. Both aryl and alkyl sodium sulfinates could
react with a wide range of 1,6-enynes to afford different
substituted benzofuran products in moderate to good yields
under mild conditions. Furthermore, benzofuran skeleton
construction and sulfonyl group introduction in a cascade
manner make this protocol more efficient and step-economic.
(
4) (a) Ivachtchenko, A. V.; Golovina, E. S.; Kadieva, M. G.; Kysil, V.
M.; Mitkin, O. D.; Tkachenko, S. E.; Okun, I. M. J. Med. Chem. 2011,
4, 8161. (b) La Regina, G.; Coluccia, A.; Brancale, A.; Piscitelli, F.;
5
Gatti, V.; Maga, G.; Samuele, A.; Pannecouque, C.; Schols, D.;
Balzarini, J.; Novellino, E.; Silvestri, R. J. Med. Chem. 2011, 54, 1587.
(c) Liu, K. G.; Robichaud, A. J.; Bernotas, R. C.; Yan, Y.; Lo, J. R.;
Zhang, M.-Y.; Hughes, Z. A.; Huselton, C.; Zhang, G. M.; Zhang, J. Y.;
Kowal, D. M.; Smith, D. L.; Schechter, L. E.; Comery, T. A. J. Med.
Chem. 2010, 53, 7639.
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(5) (a) Ulman, A.; Willand, C. S.; Kohler, W.; Robello, D. R.;
Williams, D. J.; Handley, L. J. Am. Chem. Soc. 1990, 112, 7083.
Mechanistic studies including radical capture reactions and O-
labeled experiments have been conducted to clarify the reaction
pathways. Further applications of this reaction are currently
underway in our laboratory.
(
b) Huang, Y.; Huo, L.; Zhang, S.; Guo, X.; Han, C. C.; Li, Y.; Hou, J.
Chem. Commun. 2011, 47, 8904.
6) (a) Michaelis, D. J.; Ischay, M. A.; Yoon, T. P. J. Am. Chem. Soc.
008, 130, 6610. (b) Zhu, Y.; Lu, W.-T.; Sun, H.-C.; Zhan, Z.-P. Org.
(
2
ASSOCIATED CONTENT
Supporting Information
Lett. 2013, 15, 4146. (c) Wu, Z.; Song, H.; Cui, X.; Pi, C.; Du, W.; Wu,
Y. Org. Lett. 2013, 15, 1270. (d) Chang, M.-Y.; Cheng, Y.-C.; Lu, Y.-J.
Org. Lett. 2014, 16, 6252. (e) Qiao, H.; Sun, S.; Yang, F.; Zhu, Y.; Zhu,
W.; Dong, Y.; Wu, Y.; Kong, X.; Jiang, L.; Wu, Y. Org. Lett. 2015, 17,
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*
S
6
086. (f) Zhang, J.; Shao, Y.; Wang, H.; Luo, Q.; Chen, J.; Xu, D.;
Wan, X. Org. Lett. 2014, 16, 3312.
Experimental section, characterization of all compounds,
copies of H and C NMR spectra for selected
(7) Yu, X.; Xin, X.; Wan, B.; Li, X. J. Org. Chem. 2013, 78, 4895.
(8) Raushel, J.; Fokin, V. V. Org. Lett. 2010, 12, 4952.
1
13
(
9) Du, B.; Qian, P.; Wang, Y.; Mei, H.; Han, J.; Pan, Y. Org. Lett.
016, 18, 4144.
10) (a) Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395.
b) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644. (c) Ziegert, R.
E.; Torang, J.; Knepper, K.; Brase, S. J. Comb. Chem. 2005, 7, 147.
2
(
Crystallographic data (CIF)
(
AUTHOR INFORMATION
■
*
*
(
(
d) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670.
e) Carlsson, B.; Singh, B. N.; Temciuc, M.; Nilsson, S.; Li, Y.-L.;
ORCID
Mellin, C.; Malm, J. J. Med. Chem. 2002, 45, 623. (f) Baba, K.;
Takeuchi, K.; Doi, M.; Inoue, M.; Kozawa, M. Chem. Pharm. Bull.
1986, 34, 1540. (g) Zhou, T.; Zhang, S.-W.; Liu, S.-S.; Cong, H.-J.;
Xuan, L.-J. Phytochem. Lett. 2010, 3, 242. (h) Flynn, B. L.; Gill, G. S.;
Grobelny, D. W.; Chaplin, J. H.; Paul, D.; Leske, A. F.; Lavranos, T.
C.; Chalmers, D. K.; Charman, S. A.; Kostewicz, E.; Shackleford, D.
M.; Morizzi, J.; Hamel, E.; Jung, M. K.; Kremmidiotis, G. J. Med. Chem.
Notes
The authors declare no competing financial interest.
2
(
011, 54, 6014.
11) (a) Yuan, H.; Bi, K.-J.; Li, B.; Yue, R.-C.; Ye, J.; Shen, Y.-H.;
Shan, L.; Jin, H.-Z.; Sun, Q.-Y.; Zhang, W.-D. Org. Lett. 2013, 15, 4742.
b) Huang, X.-C.; Liu, Y.-L.; Liang, Y.; Pi, S.-F.; Wang, F.; Li, J.-H.
ACKNOWLEDGMENTS
■
The authors thank the National Key Research and Develop-
ment Program of China (2016YFA0602900), the National
Natural Science Foundation of China (21672072, 21472051
and 21490572), Pearl River S&T Nova Program of Guangzhou
(
Org. Lett. 2008, 10, 1525. (c) Wan, J.-P.; Wang, H.; Liu, Y.; Ding, H.
Org. Lett. 2014, 16, 5160. (d) Liu, J.; Liu, Z.; Liao, P.; Bi, X. Org. Lett.
2014, 16, 6204. (e) Liu, Y.; Qian, J.; Lou, S.; Xu, Z. J. Org. Chem. 2010,
7
5, 6300. (f) Liang, Z.; Hou, W.; Du, Y.; Zhang, Y.; Pan, Y.; Mao, D.;
Zhao, K. Org. Lett. 2009, 11, 4978.
12) (a) Hu, M.; Song, R.-J.; Ouyang, X.-H.; Tan, F.-L.; Wei, W.-T.;
(
201610010160) for financial support.
(
REFERENCES
■
Li, J.-H. Chem. Commun. 2016, 52, 3328. (b) Hu, M.; Song, R.-J.; Li, J.-
H. Angew. Chem., Int. Ed. 2015, 54, 608. (c) Sakiyama, N.; Noguchi,
K.; Tanaka, K. Angew. Chem., Int. Ed. 2012, 51, 5976. (d) Zhao, K.;
Zhi, Y.; Shu, T.; Valkonen, A.; Rissanen, K.; Enders, D. Angew. Chem.,
Int. Ed. 2016, 55, 12104.
(
1) (a) Williams, T. M.; Ciccarone, T. M.; MacTough, S. C.; Rooney,
C. S.; Balani, S. K.; Condra, J. H.; Emini, E. A.; Goldman, M. E.;
Greenlee, W. J.; Kauffman, L. R.; O’Brien, J. A.; Sardana, V. V.; Schleif,
W. A.; Theoharides, A. D.; Anderson, P. S. J. Med. Chem. 1993, 36,
291. (b) Barbuceanu, S.-F.; Almajan, G. L.; Saramet, I.; Draghici, C.;
Tarcomnicu, A. I.; Bancescu, G. Eur. J. Med. Chem. 2009, 44, 4752.
c) Hartz, R. A.; Arvanitis, A. G.; Arnold, C.; Rescinito, J. P.; Hung, K.
L.; Zhang, G.; Wong, H.; Langley, D. R.; Gilligan, P. J.; Trainor, G. L.
Bioorg. Med. Chem. Lett. 2006, 16, 934.
2) (a) Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Organo-
metallics 1996, 15, 3189. (b) Beletskaya, I. P.; Ananikov, V. P. Chem.
1
(13) (a) Tang, X.; Huang, L.; Qi, C.; Wu, X.; Wu, W.; Jiang, H.
Chem. Commun. 2013, 49, 6102. (b) Xu, Y.; Tang, X.; Hu, W.; Wu,
W.; Jiang, H. Green Chem. 2014, 16, 3720. (c) Li, X.; Xu, Y.; Wu, W.;
Jiang, C.; Qi, C.; Jiang, H. Chem. - Eur. J. 2014, 20, 7911. (d) Tang, X.;
Huang, L.; Xu, Y.; Yang, J.; Wu, W.; Jiang, H. Angew. Chem., Int. Ed.
(
(
2
014, 53, 4205. (e) Xu, Y.; Zhao, J.; Tang, X.; Wu, W.; Jiang, H. Adv.
Synth. Catal. 2014, 356, 2029. (f) Wu, W.; Yi, S.; Yu, Y.; Huang, W.;
Jiang, H. J. Org. Chem. 2017, 82, 1224.
Rev. 2011, 111, 1596. (c) Liu, G.; Fan, C.; Wu, J. Org. Biomol. Chem.
015, 13, 1592. (d) Noshi, M. N.; El-awa, A.; Torres, E.; Fuchs, P. L. J.
2
Am. Chem. Soc. 2007, 129, 11242. (e) Vedula, M. S.; Pulipaka, A. B.;
Venna, C.; Chintakunta, V. K.; Jinnapally, S.; Kattuboina, V. A.;
Vallakati, R. K.; Basetti, V.; Akella, V.; Rajgopal, S.; Reka, A. K.;
Teepireddy, S. K.; Mamnoor, P. K.; Rajagopalan, R.; Bulusu, G.;
D
Org. Lett. XXXX, XXX, XXX−XXX