Organic Letters
Letter
(10) For other methods, see: (a) Xu, Q.; Dai, L.; You, S. Chem. Sci.
2013, 4, 97. (b) Hellal, M.; Singh, S.; Cuny, G. D. J. Org. Chem. 2012,
77, 4123. (c) Lim, H. J.; Gallucci, J. C.; RajanBabu, T. V. Org. Lett.
2010, 12, 2162. (d) Kalinin, A. V.; Chauder, B. A.; Rakhit, S.; Snieckus,
V. Org. Lett. 2003, 5, 3519. (e) Katayama, S.; Ae, N.; Nagata, R. J. Org.
Chem. 2001, 66, 3474. (f) Horwell, D. C.; Nichols, P. D.; Ratcliffe, G.
S.; Roberts, E. J. Org. Chem. 1994, 59, 4418. (g) Lauchli, R.; Shea, K. J.
Org. Lett. 2006, 8, 5287. (h) Bur, S. K.; Padwa, A. Org. Lett. 2002, 4,
(16) (a) Hou, W.; Zhou, B.; Yang, Y.; Feng, H.; Li, Y. Org. Lett. 2013,
15, 1814. (b) Zhou, B.; Hou, W.; Yang, Y.; Li, Y. Chem.Eur. J. 2013,
19, 4701. (c) Zhou, B.; Yang, Y.; Shi, J.; Feng, H.; Li, Y. Chem.Eur. J.
2013, 19, 10511. (d) Zhou, B.; Du, J.; Yang, Y.; Feng, H.; Li, Y. Org.
Lett. 2013, 15, 6302. (e) Zhou, B.; Yang, Y.; Lin, S.; Li, Y. Adv. Synth.
Catal. 2013, 355, 360. (f) Zhou, B.; Du, J.; Yang, Y.; Feng, H.; Li, Y.
Org. Lett. 2014, 16, 592. (g) Yang, Y.; Hou, W.; Qin, L.; Du, J.; Feng,
H.; Zhou, B.; Li, Y. Chem.Eur. J. 2014, 20, 416. (h) Zhou, B.; Yang,
Y.; Li, Y. Chem. Commun. 2012, 48, 5163. (i) Zhou, B.; Du, J.; Yang,
Y.; Li, Y. Org. Lett. 2013, 15, 2934. (j) Yang, Y.; Zhou, B.; Li, Y. Adv.
Synth. Catal. 2012, 354, 2916. (k) Du, J.; Yang, Y.; Feng, H.; Li, Y.;
Zhou, B. Chem.Eur. J. 2014, 20, 5727. (l) Du, J.; Zhou, B.; Yang, Y.;
Li, Y. Chem.Asian J. 2013, 8, 1386.
4135. (i) Schcņ herr, H.; Leighton, J. L. Org. Lett. 2012, 14, 2610.
(j) Cheng, D.-J.; Wu, H.-B.; Tian, S.-K. Org. Lett. 2011, 13, 5636.
(k) Greshock, T. J.; Funk, R. L. J. Am. Chem. Soc. 2006, 128, 4946.
(11) Park, I.-K.; Park, J.; Cho, C.-G. Angew. Chem., Int. Ed. 2012, 51,
2496.
(17) During our manuscript preparation, a Rh-catalyzed intra-
molecular oxidative annulation reaction of a tethered alkyne was
reported; see: (a) Zhang, X.; Li, Y.; Shi, H.; Zhang, L.; Zhang, S.; Xu,
X.; Liu, Q. Chem. Commun. 2014, 50, 7306. (b) Tao, P.; Jia, Y. Chem.
Commun. 2014, 50, 7367.
(12) (a) Breazzano, S. P.; Poudel, Y. B.; Boger, D. L. J. Am. Chem.
Soc. 2013, 135, 1600. (b) Shan, D.; Gao, Y.; Jia, Y. Angew. Chem., Int.
Ed. 2013, 52, 4902.
(13) For reviews on Rh(III) catalyzed C−H activation, see:
(a) Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008,
41, 1013. (b) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev.
2010, 110, 624. (c) Bouffard, J.; Itami, K. Top. Curr. Chem. 2010, 292,
231. (d) Satoh, T.; Miura, M. Chem.Eur. J. 2010, 16, 11212.
(e) Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem.
Res. 2012, 45, 814. (f) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012,
41, 3651. (g) Patureau, F. W.; Wencel-Delord, J.; Glorius, F.
Aldrichimica Acta 2012, 45, 31. For reviews on other transition-
metal-catalyzed C−H activation: (h) Ackermann, L.; Vicente, R.;
Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792.
(18) For rhodium-catalyzed C−H activation using oxidizing directing
groups, see: (a) Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem.
Soc. 2010, 132, 6908. (b) Too, P. C.; Wang, Y.-F.; Chiba, S. Org. Lett.
2010, 12, 5688. (c) Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am.
Chem. Soc. 2011, 133, 6449. (d) Rakshit, S.; Grohmann, C.; Besset, T.;
Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350. (e) Too, P. C.; Chua, S.
H.; Wong, S. H.; Chiba, S. J. Org. Chem. 2011, 76, 6159. (f) Zhang, X.;
Chen, D.; Zhao, M.; Zhao, J.; Jia, A.; Li, X. Adv. Synth. Catal. 2011,
353, 719. (g) Hyster, T. K.; Rovis, T. Chem. Commun. 2011, 47,
11846. (h) Wang, H.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51,
7318. (i) Hyster, T. K.; KnÅrr, L.; Ward, T. R.; Rovis, T. Science 2012,
338, 500. (j) Ye, B.; Cramer, N. Science 2012, 338, 504. (k) Wang, H.;
Grohmann, C.; Nimphius, C.; Glorius, F. J. Am. Chem. Soc. 2012, 134,
19592. (l) Neely, J. M.; Rovis, T. J. Am. Chem. Soc. 2013, 135, 66.
(m) Hyster, T. K.; Ruhl, K. E.; Rovis, T. J. Am. Chem. Soc. 2013, 135,
5364. (n) Liu, G.; Shen, Y.; Zhou, Z.; Lu, X. Angew. Chem., Int. Ed.
2013, 52, 6033. (o) Qi, Z.; Wang, M.; Li, X. Org. Lett. 2013, 15, 5440.
(p) Liu, B.; Song, C.; Sun, C.; Zhou, S.; Zhu, J. J. Am. Chem. Soc. 2013,
135, 16625. (q) Zhao, D.; Shi, Z.; Glorius, F. Angew. Chem., Int. Ed.
2013, 52, 12426. (r) Wang, C.; Huang, Y. Org. Lett. 2013, 15, 5294.
(14) For selected Rh(III)-catalyzed C−H functionalization by using
alkynes and alkenes as substrates, see: (a) Liu, B.; Fan, Y.; Gao, Y.;
Sun, C.; Xu, C.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 468. (b) Feng, C.;
Feng, D.; Loh, T.-P. Org. Lett. 2013, 15, 3670. (c) Wang, H.; Schroder,
N.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 5386. (d) Wang, H.;
Grohmann, C.; Nimphius, C.; Glorius, F. J. Am. Chem. Soc. 2012, 134,
19592. (e) Zhen, W.; Wang, F.; Zhao, M.; Du, Z.; Li, X. Angew. Chem.,
Int. Ed. 2012, 51, 11819. (f) Li, B.-J.; Wang, H.-Y.; Zhu, Q.-L.; Shi, Z.-
J. Angew. Chem., Int. Ed. 2012, 51, 3948. (g) Wang, D.; Wang, F.; Song,
G.; Li, X. Angew. Chem., Int. Ed. 2012, 51, 12348. (h) Zhang, J.; Loh,
T.-P. Chem. Commun. 2012, 48, 11232. (i) Ye, B.; Cramer, N. Science
2012, 338, 504. (j) Patureau, F. W.; Besset, T.; Kuhl, N.; Glorius, F. J.
Am. Chem. Soc. 2011, 133, 2154. (k) Guimond, N.; Gorelsky, S. I.;
Fagnou, K. J. Am. Chem. Soc. 2011, 133, 6449. (l) Li, H.; Li, Y.; Zhang,
X.-S.; Chen, K.; Wang, X.; Shi, Z.-J. J. Am. Chem. Soc. 2011, 133,
15244. (m) Patureau, F. W.; Glorius, F. Angew. Chem., Int. Ed. 2011,
50, 1977. (n) Too, P. C.; Wang, Y.-F.; Chiba, S. Org. Lett. 2010, 12,
5688. (o) Rakshit, S.; Grohmann, C.; Besset, T.; Glorius, F. J. Am.
Chem. Soc. 2011, 133, 2350. (p) Hyster, T. K.; Rovis, T. J. Am. Chem.
Soc. 2010, 132, 10565. (q) Rakshit, S.; Patureau, F. W.; Glorius, F. J.
Am. Chem. Soc. 2010, 132, 9585. (r) Guimond, N.; Fagnou, K. J. Am.
Chem. Soc. 2009, 131, 12050. (s) Umeda, N.; Tsurugi, H.; Satoh, T.;
Miura, M. Angew. Chem., Int. Ed. 2008, 47, 4019. (t) Pham, M. V.; Ye,
B.; Cramer, N. Angew. Chem., Int. Ed. 2012, 51, 10610. (u) Ueura, K.;
Satoh, T.; Miura, M. Org. Lett. 2007, 9, 1407. (v) Ueura, K.; Satoh, T.;
Miura, M. J. Org. Chem. 2007, 72, 5362. For intramolecular reaction:
(w) Xu, X.; Liu, Y.; Park, C.-M. Angew. Chem., Int. Ed. 2012, 51, 9372.
(x) Davis, T. A.; Hyster, T. K.; Rovis, T. Angew. Chem., Int. Ed. 2013,
52, 14181. (y) Ye, B.; Donets, P. A.; Cramer, N. Angew. Chem., Int. Ed.
2014, 53, 507. (z) Shi, Z.; Boultadakis-Arapinis, M.; Koester, D. C.;
Glorius, F. Chem. Commun. 2014, 50, 2650.
(15) For Rh(III)-catalyzed oxidative indole synthesis: (a) Stuart, D.
R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. J. Am. Chem.
Soc. 2008, 130, 16474. (b) Stuart, D. R.; Alsabeh, P.; Kuhn, M.;
Fagnou, K. J. Am. Chem. Soc. 2010, 132, 18326. (c) Chen, J.; Song, G.;
Pan, C.-L.; Li, X. Org. Lett. 2010, 12, 5426. (d) Huestis, M. P.; Chan,
L. N.; Stuart, D. R.; Fagnou, K. Angew. Chem., Int. Ed. 2011, 50, 1338.
(e) Hoshino, Y.; Shibata, Y.; Tanaka, K. Adv. Synth. Catal. 2014, 356,
1577. (f) Shibata, Y.; Tanaka, K. Angew. Chem., Int. Ed. 2011, 50,
10917. For Ru(II) catalyzed indole synthesis, see: (g) Ackermann, L.;
Lygin, A. V. Org. Lett. 2012, 14, 764.
3903
dx.doi.org/10.1021/ol501599j | Org. Lett. 2014, 16, 3900−3903