Organic Letters
Letter
Shea, K. J. Org. Lett. 2006, 8, 5287−5289. (f) Coldham, I.; Dobson, B.
C.; Fletcher, S. R.; Franklin, A. I. Eur. J. Org. Chem. 2007, 2007,
Scheme 5. Possible Reaction Pathway
2
(
1
676−2686.
5) (a) Fischer, O.; Mu
09, 69−87. (b) Vilsmeier, A.; Haack, A. Ber. Dtsch. Chem. Ges. B
927, 60, 119−122. (c) Meth-Cohn, O.; Stanforth, S. P. Comp. Org.
̈
ller, A.; Vilsmeier, A. J. Prakt. Chem. 1925,
1
Synth. 1991, 2, 777−794. (d) Seybold, G. J. Prakt. Chem./Chem.-Ztg.
1
4
6
996, 338, 392−396. (e) Jones, G.; Stanforth, S. P. Org. React. 1996,
9, 1−330. (f) Jones, G.; Stanforth, S. P. Org. React. 2000, 56, 355−
86.
(
6) (a) Reimer, K. Ber. Dtsch. Chem. Ges. 1876, 9, 423−424.
b) Reimer, K.; Tiemann, F. Ber. Dtsch. Chem. Ges. 1876, 9, 824−828.
c) Reimer, K.; Tiemann, F. Ber. Dtsch. Chem. Ges. 1876, 9, 1268−
(
(
1
278. (d) Wynberg, H. Chem. Rev. 1960, 60, 169−184. (e) Wynberg,
H.; Meijer, E. W. Org. React. 1982, 28, 1−36. (f) Wynberg, H. Comp.
Org. Synth. 1991, 2, 769−775.
(
7) (a) Rieche, A.; Gross, H.; Ho
b) Rieche, A.; Gross, H.; Ho
8) (a) Duff, J. C.; Bills, E. J. J. Chem. Soc. 1932, 0, 1987−1988.
̈
ft, E. Chem. Ber. 1960, 93, 88−94.
(
(
̈
ft, E. Org. Synth. 1967, 47, 1−3.
(
b) Duff, J. C.; Bills, E. J. J. Chem. Soc. 1934, 0, 1305−1308. (c) Duff,
J. C.; Bills, E. J. J. Chem. Soc. 1941, 0, 547−550. (d) Duff, J. C.; Bills,
E. J. J. Chem. Soc. 1945, 0, 276−277. (e) Ferguson, L. N. Chem. Rev.
1
(
946, 38, 227−254.
9) (a) James, P.; Snyder, H. Org. Synth. 1959, 39, 30−33.
substrate scope, including N-substituted indoles as well as free
NH-indoles, with an excellent functional group tolerance. The
gram-scale experiment has shown great potential in the
synthetic utility of this transformation. Further investigations
into the mechanistic details and synthetic applications are
currently underway in our laboratory.
(b) Rodriguez, J. G.; Lafuente, A.; Garcïa-Almaraz, P. J. Heterocycl.
Chem. 2000, 37, 1281−1288. (c) Jones, G.; Stanforth, S. P. Organic
Reactions; John Wiley & Sons, Inc.: 2004. (d) Pruger, B.; Bach, T.
̈
Synthesis 2007, 2007, 1103−1106. (e) Xu, H.; Fan, L.-L. Eur. J. Med.
Chem. 2011, 46, 364−369.
(
(
10) Blume, R. C.; Lindwall, H. G. J. Org. Chem. 1945, 10, 255−258.
11) van Niel, M. B.; Collins, I.; Beer, M. S.; Broughton, H. B.;
Cheng, S. K.; Goodacre, S. C.; Heald, A.; Locker, K. L.; MacLeod, A.
M.; Morrison, D.; Moyes, C. R.; O’Connor, D.; Pike, A.; Rowley, M.;
Russell, M. G. N.; Sohal, B.; Stanton, J. A.; Thomas, S.; Verrier, H.;
Watt, A. P.; Castro, J. L. J. Med. Chem. 1999, 42, 2087−2104.
ASSOCIATED CONTENT
Supporting Information
■
*
S
(
12) Bennasar, M. L.; Zulaica, E.; Sole,
007, 63, 861−866.
13) (a) Wu, W.; Su, W. J. Am. Chem. Soc. 2011, 133, 11924−
19247. (b) Chen, J.; Liu, B.; Liu, D.; Liu, S.; Cheng, J. Adv. Synth.
́
D.; Alonso, S. Tetrahedron
2
(
Experimental procedures and spectroscopic data (PDF)
1
Catal. 2012, 354, 2438−2442. (c) Li, L. T.; Huang, J.; Li, H. Y.; Wen,
AUTHOR INFORMATION
L. J.; Wang, P.; Wang, B. Chem. Commun. 2012, 48, 5187−5189.
■
(d) Fei, H.; Yu, J.; Jiang, Y.; Guo, H.; Cheng, J. Org. Biomol. Chem.
2
2
013, 11, 7092−7095. (e) Li, X.; Gu, X.; Li, Y.; Li, P. ACS Catal.
*
ORCID
014, 4, 1897−1900. (f) Tongkhan, S.; Radchatawedchakoon, W.;
Kruanetr, S.; Sakee, U. Tetrahedron Lett. 2014, 55, 3909−3912.
(
2
g) Zhang, B.; Liu, B.; Chen, J.; Wang, J.; Liu, M. Tetrahedron Lett.
014, 55, 5618−5621. (h) Lu, L.; Xiong, Q.; Guo, S.; He, T.; Xu, F.;
Gong, J.; Zhu, Z.; Cai, H. Tetrahedron 2015, 71, 3637−3641.
i) Iranpoor, N.; Panahi, F.; Erfan, S.; Roozbin, F. J. Heterocycl. Chem.
Notes
(
The authors declare no competing financial interest.
2
017, 54, 904−910. (j) Wang, Q.-D.; Yang, J.-M.; Fang, D.; Ren, J.;
Zeng, B.-B. Tetrahedron Lett. 2017, 58, 2877−2880. (k) Zeng, B.-B.;
Yang, J.-M.; Wang, Q.-D.; Zhou, B.; Fang, D.; Ren, J. Synlett 2017, 28,
ACKNOWLEDGMENTS
■
We are grateful to the National Natural Science Foundation of
China (Grant Nos. 21672074 and 21372089) for the financial
support.
2670−2674. (l) Betterley, N. M.; Kerdphon, S.; Chaturonrutsamee,
S.; Kongsriprapan, S.; Surawatanawong, P.; Soorukram, D.;
Pohmakotr, M.; Andersson, P. G.; Reutrakul, V.; Kuhakarn, C.
Asian J. Org. Chem. 2018, 7, 1642−1647.
REFERENCES
(14) (a) Huang, H.; Li, X.; Yu, C.; Zhang, Y.; Mariano, P. S.; Wang,
■
(
1) Rudolphi, F.; Song, B.; Gooßen, L. J. Adv. Synth. Catal. 2011,
W. Angew. Chem., Int. Ed. 2017, 56, 1500−1505. (b) Huang, H.; Yu,
C.; Li, X.; Zhang, Y.; Zhang, Y.; Chen, X.; Mariano, P. S.; Xie, H.;
Wang, W. Angew. Chem., Int. Ed. 2017, 56, 8201−8205. (c) Huang,
H.; Yu, C.; Zhang, Y.; Zhang, Y.; Mariano, P. S.; Wang, W. J. Am.
Chem. Soc. 2017, 139, 9799−9802. (d) Zhang, S.; Tan, Z.; Zhang, H.;
Liu, J.; Xu, W.; Xu, K. Chem. Commun. 2017, 53, 11642−11645.
(e) Liu, Y.; Cai, L.; Xu, S.; Pu, W.; Tao, X. Chem. Commun. 2018, 54,
2166−2168. (f) Yin, Z.; Wang, Z.; Wu, X. F. Org. Biomol. Chem. 2018,
16, 3707−3710. (g) Zhao, B.; Shang, R.; Cheng, W.-M.; Fu, Y. Org.
Chem. Front. 2018, 5, 1782−1786.
3
53, 337−342.
(
(
2) Lin, D.-Z.; Huang, J.-M. Org. Lett. 2018, 20, 2112−2115.
3) Etzenbach-Effers, K.; Berkessel, A. In Asymmetric Organocatalysis;
List, B., Eds.; Springer-Verlag: Berlin, Heidelberg, 2010.
4) (a) Gribble, G. W.; Pelcman, B. J. Org. Chem. 1992, 57, 3636−
642. (b) Macor, J. E.; Blank, D. H.; Fox, C. B.; Lebel, L. A.;
Newman, M. E.; Post, R. J.; Ryan, K.; Schmidt, A. W.; Schulz, D. W.;
Koe, B. K. J. Med. Chem. 1994, 37, 2509−2512. (c) Ziegler, F. E.;
Belema, M. J. Org. Chem. 1997, 62, 1083−1094. (d) Tohyama, S.;
Choshi, T.; Matsumoto, K.; Yamabuki, A.; Ikegata, K.; Nobuhiro, J.;
Hibino, S. Tetrahedron Lett. 2005, 46, 5263−5264. (e) Lauchli, R.;
(
3
(15) (a) Moeller, K. D. Tetrahedron 2000, 56, 9527−9554.
(b) Lund, H. J. Electrochem. Soc. 2002, 149, S21−S33. (c) Sperry, J.
D
Org. Lett. XXXX, XXX, XXX−XXX