ACS Catalysis
Research Article
(7) (a) Zhang, X.; Qi, Z.; Li, X. Angew. Chem., Int. Ed. 2014, 53,
10794−10798. (b) Sharma, U.; Park, Y.; Chang, S. J. Org. Chem. 2014,
79, 9899−9906. (c) Dateer, R. B.; Chang, S. J. Am. Chem. Soc. 2015,
137, 4908−4911. (d) Yan, H.; Wang, H.; Li, X.; Xin, X.; Wang, C.;
Wan, B. Angew. Chem., Int. Ed. 2015, 54, 10613−10617. (e) Zhou, Z.;
Liu, G.; Chen, Y.; Lu, X. Adv. Synth. Catal. 2015, 357, 2944−2950.
(f) Kong, L.; Xie, F.; Yu, S.; Qi, Z.; Li, X. Chin. J. Catal. 2015, 36, 925−
932.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work was supported by the grants of the National Natural
Science Foundation of China (21372121 and 21421062).
(8) (a) Li, B.; Feng, H.; Xu, S.; Wang, B. Chem. - Eur. J. 2011, 17,
12573−12577. (b) Tan, X.; Liu, B.; Li, X.; Li, B.; Xu, S.; Song, H.;
Wang, B. J. Am. Chem. Soc. 2012, 134, 16163−16166. (c) Li, B.; Feng,
H.; Wang, N.; Ma, J.; Song, H.; Xu, S.; Wang, B. Chem. - Eur. J. 2012,
18, 12873−12879. (d) Wang, N.; Li, B.; Song, H.; Xu, S.; Wang, B.
Chem. - Eur. J. 2013, 19, 358−364. (e) Li, B.; Wang, N.; Liang, Y.; Xu,
S.; Wang, B. Org. Lett. 2013, 15, 136−139. (f) Li, B.; Yang, J.; Xu, H.;
Song, H.; Wang, B. J. Org. Chem. 2015, 80, 12397−12409.
(9) (a) Ishikura, M.; Abe, T.; Choshi, T.; Hibino, S. Nat. Prod. Rep.
2013, 30, 694−752. (b) Patil, S. A.; Patil, R.; Miller, D. D. Future Med.
Chem. 2012, 4, 2085−2115. (c) Kochanowska-Karamyan, A. J.;
Hamann, M. T. Chem. Rev. 2010, 110, 4489−4497. (d) Somei, M.;
Yamada, F. Nat. Prod. Rep. 2005, 22, 73−103. (e) Kawasaki, T.;
Higuchi, K. Nat. Prod. Rep. 2005, 22, 761−793. (f) Eicher, T.;
Hauptmann, S. The Chemistry of Heterocycles: Structure, Reactions,
Syntheses, and Applications, 2nd ed., Wiley-VCH: Weinheim, 2003.
(g) Sundberg, R. J. Indoles; Academic Press: San Diego, 1996.
(10) For recent reviews on indole synthesis, see: (a) Guo, T.; Huang,
F.; Yu, L.; Yu, Z. Tetrahedron Lett. 2015, 56, 296−302. (b) Inman, M.;
Moody, C. J. Chem. Sci. 2013, 4, 29−41. (c) Shiri, M. Chem. Rev. 2012,
112, 3508−3549. (d) Cacchi, S.; Fabrizi, G. Chem. Rev. 2011, 111,
PR215−PR283. (e) Vicente, R. Org. Biomol. Chem. 2011, 9, 6469−
6480. (f) Taber, D. F.; Tirunahari, P. K. Tetrahedron 2011, 67, 7195−
7210.
REFERENCES
■
(1) For selected recent reviews, see: (a) Song, G.; Li, X. Acc. Chem.
Res. 2015, 48, 1007−1020. (b) Huang, H.; Ji, X.; Wu, W.; Jiang, H.
Chem. Soc. Rev. 2015, 44, 1155−1171. (c) Kuhl, N.; Schroder, N.;
Glorius, F. Adv. Synth. Catal. 2014, 356, 1443−1460. (d) Rouquet, G.;
Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726−11743. (e) Colby,
D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012,
45, 814−825. (f) Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem.
Rev. 2012, 112, 5879−5918. (g) Song, G.; Wang, F.; Li, X. Chem. Soc.
Rev. 2012, 41, 3651−3678. (h) Kuhl, N.; Hopkinson, M. N.; Wencel-
Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236−10254.
(i) Li, B.-J.; Shi, Z.-J. Chem. Soc. Rev. 2012, 41, 5588−5598. (j) Engle,
K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788−
802. (k) Neufeldt, S. R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936−
946. (l) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev.
2011, 40, 5068−5083. (m) Yeung, C. S.; Dong, V. M. Chem. Rev.
2011, 111, 1215−1292. (n) Wencel-Delord, J.; Droge, T.; Liu, F.;
̈
Glorius, F. Chem. Soc. Rev. 2011, 40, 4740−4761. (o) Mkhalid, I. A. I.;
Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev.
2010, 110, 890−931.
(2) For selected reviews, see: (a) Wencel-Delord, J.; Glorius, F. Nat.
Chem. 2013, 5, 369−375. (b) Yamaguchi, J.; Yamaguchi, A. D.; Itami,
K. Angew. Chem., Int. Ed. 2012, 51, 8960−9009. (c) Chen, X.; Engle,
K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094−
5115.
(11) For selective examples on indole synthesis via metal-catalyzed
(3) (a) Shi, R.; Lu, L.; Zhang, H.; Chen, B.; Sha, Y.; Liu, C.; Lei, A.
Angew. Chem., Int. Ed. 2013, 52, 10582−10585. (b) Huang, X.; Huang,
J.; Du, C.; Zhang, X.; Song, F.; You, J. Angew. Chem., Int. Ed. 2013, 52,
12970−12974. (c) Zhou, B.; Chen, Z.; Yang, Y.; Ai, W.; Tang, H.; Wu,
Y.; Zhu, W.; Li, Y. Angew. Chem., Int. Ed. 2015, 54, 12121−12126.
(4) (a) Liang, M.; Chen, J. Chem. Soc. Rev. 2013, 42, 3453−3488.
C−H activation/annulation with alkynes, see: (a) Wang, H.; Moselage,
́
M.; Gonzalez, M. J.; Ackermann, L. ACS Catal. 2016, 6, 2705−2709.
(b) Yang, Y.; Wang, X.; Li, Y.; Zhou, B. Angew. Chem., Int. Ed. 2015,
54, 15400−15404. (c) Wu, J.-Q.; Yang, Z.; Zhang, S.-S.; Jiang, C.-Y.;
Li, Q.; Huang, Z.-S.; Wang, H. ACS Catal. 2015, 5, 6453−6457.
(d) Fan, Z.; Song, S.; Li, W.; Geng, K.; Xu, Y.; Miao, Z. H.; Zhang, A.
Org. Lett. 2015, 17, 310−313. (e) Hoshino, Y.; Shibata, Y.; Tanaka, K.
Adv. Synth. Catal. 2014, 356, 1577−1585. (f) Zhang, G.; Yu, H.; Qin,
G.; Huang, H. Chem. Commun. 2014, 50, 4331−4334. (g) Zhou, B.;
Yang, Y.; Tang, H.; Du, J.; Feng, H.; Li, Y. Org. Lett. 2014, 16, 3900−
3903. (h) Zheng, L.; Hua, R. Chem. - Eur. J. 2014, 20, 2352−2356.
(i) Cai, S.; Yang, K.; Wang, D. Z. Org. Lett. 2014, 16, 2606−2609.
(j) Wang, C.; Sun, H.; Fang, Y.; Huang, Y. Angew. Chem., Int. Ed. 2013,
52, 5795−5798. (k) Liu, B.; Song, C.; Sun, C.; Zhou, S.; Zhu, J. J. Am.
Chem. Soc. 2013, 135, 16625−16631. (l) Zhao, D.; Shi, Z.; Glorius, F.
Angew. Chem., Int. Ed. 2013, 52, 12426−12429. (m) Ackermann, L.;
Lygin, A. V. Org. Lett. 2012, 14, 764−767. (n) Huestis, M. P.; Chan,
L.; Stuart, D. R.; Fagnou, K. Angew. Chem., Int. Ed. 2011, 50, 1338−
1341. (o) Chen, J.; Pang, Q.; Sun, Y.; Li, X. J. Org. Chem. 2011, 76,
3523−3526. (p) Chen, J.; Song, G.; Pan, C. L.; Li, X. Org. Lett. 2010,
12, 5426−5429. (q) Stuart, D. R.; Alsabeh, P.; Kuhn, M.; Fagnou, K. J.
Am. Chem. Soc. 2010, 132, 18326−18339. (r) Shi, Z.; Zhang, C.; Li, S.;
Pan, D.; Ding, S.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48,
4572−4576. (s) Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.;
Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474−16475 and references
cited therein and also see refs 7d−f..
́
(b) Ruiz-Sanchis, P.; Savina, S. A.; Albericio, F.; Alvarez, M. Chem. -
Eur. J. 2011, 17, 1388−1408. (c) Hagfeldt, A.; Boschloo, G.; Sun, L.;
Kloo, L.; Pettersson, H. Chem. Rev. 2010, 110, 6595−6663. (d) Chen,
C.-T. Chem. Mater. 2004, 16, 4389−4400. (e) Wermuth, C.-G. The
Practice of Medicinal Chemistry, 3rd ed., Academic Press: London,
2008.
(5) For selected reviews, see: (a) Ouyang, K.; Hao, W.; Zhang, W.-
X.; Xi, Z. Chem. Rev. 2015, 115, 12045−12090. (b) Wang, R.; Falck, J.
R. RSC Adv. 2014, 4, 1062−1066. (c) Li, Y.; Ma, L.; Li, Z. Youji
Huaxue 2013, 33, 704−714. (d) Turner, N. J. Chem. Rev. 2011, 111,
4073−4087. (e) Kruger, K.; Tillack, A.; Beller, M. ChemSusChem
̈
2009, 2, 715−717.
(6) For selective examples, see: (a) Ueno, S.; Chatani, N.; Kakiuchi,
F. J. Am. Chem. Soc. 2007, 129, 6098−6099. (b) Chen, Y.; Cho, C.-H.;
Larock, R. C. Org. Lett. 2009, 11, 173−176. (c) Li, H.; He, Z.; Guo, X.;
Li, W.; Zhao, X.; Li, Z. Org. Lett. 2009, 11, 4176−4179. (d) Zeng, X.;
Kinjo, R.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2010, 49,
942−945. (e) Kuninobu, Y.; Nishi, M.; Takai, K. Chem. Commun.
2009, 46, 8860−8862. (f) Xia, X.-F.; Zhang, L.-L.; Song, X.-R.; Niu, Y.-
N.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun. 2013, 49, 1410−1412.
(g) Zhang, X.; Yang, W.; Wang, L. Org. Biomol. Chem. 2013, 11,
3649−3654. (h) Yao, B.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed.
2013, 52, 12992−12996. (i) Zhao, Y.; Snieckus, V. Org. Lett. 2014, 16,
3200−3203. (j) Chen, X.; Chen, T.; Li, Q.; Zhou, Y.; Han, L.-B.; Yin,
S.-F. Chem. - Eur. J. 2014, 20, 12234−12238. (k) Pan, X.; Luo, Y.;
Kuang, Y.; Li, G. Org. Biomol. Chem. 2014, 12, 5861−5865. (l) Sheng,
J.; Li, S.; Wu, J. Chem. Commun. 2014, 50, 578−580. (m) Bao, Y.-S.;
Zhaorigetu, B.; Agula, B.; Baiyin, M.; Jia, M. J. Org. Chem. 2014, 79,
803−808. (n) Ha, T. M.; Yao, B.; Wang, Q.; Zhu, J. Org. Lett. 2015,
17, 1750−1753.
(12) CsOAc has been utilized as an additive in many Rh(III)-
catalyzed C−H functionalization to facilitate C−H activation step, for
selective examples, see: (a) Qi, Z.; Yu, S.; Li, X. Org. Lett. 2016, 18,
700−703. (b) Hyster, T. K.; Dalton, D. M.; Rovis, T. Chem. Sci. 2015,
6, 254−258. (c) Hyster, T. K.; Ruhl, K. E.; Rovis, T. J. Am. Chem. Soc.
2013, 135, 5364−5367. (d) Liu, G.; Shen, Y.; Zhou, Z.; Lu, X. Angew.
Chem., Int. Ed. 2013, 52, 6033−6037. (e) Cui, S.; Zhang, Y.; Wu, Q.
Chem. Sci. 2013, 4, 3421−3426. (f) Wang, H.; Glorius, F. Angew.
Chem., Int. Ed. 2012, 51, 7318−7322. (g) Zeng, R.; Fu, C.; Ma, S. J.
3861
ACS Catal. 2016, 6, 3856−3862