Organic Letters
Letter
Chem. Lett. 2007, 17, 4646−4649. (c) Nguyen, T. T. B.; Lomberget,
T.; Tran, N. C.; Colomb, E.; Nachtergaele, L.; Thoret, S.; Dubois, J.;
Abdayem, R.; Haftek, M.; Barret, R. Bioorg. Med. Chem. Lett. 2012, 22,
7227−7231. (d) Gore, V.; Gravel, S.; Cossette, C.; Patel, P.; Chourey,
S.; Ye, Q.; Rokach, J.; Powell, W. S. J. Med. Chem. 2014, 57, 364−377.
(7) For some selected references, see: (a) Bergman, J.; Desarbre, E.
Synlett 1997, 603−605. (b) Abbiati, G.; Canevari, V.; Facoetti, D.;
1889. See also: (c) Rutherford, J. L.; Rainka, M. P.; Buchwald, S. L. J.
Am. Chem. Soc. 2002, 124, 15168−15169. (d) Yamazaki, K.;
Nakamura, Y.; Kondo, Y. J. Org. Chem. 2003, 68, 6011−6019.
(e) Barolo, S. M.; Lukach, A. E.; Rossi, R. A. J. Org. Chem. 2003, 68,
2807−2811. (f) Nazare, M.; Schneider, C.; Lindenschmidt, A.; Will, D.
́
W. Angew. Chem., Int. Ed. 2004, 43, 4526−4528. (g) Sole, D.; Serrano,
O. J. Org. Chem. 2008, 73, 2476−2479. (h) Ali, M. A.; Punniyamurthy,
T. Synlett 2011, 623−626. (i) Nguyen, H. H.; Kurth, M. J. Org. Lett.
2013, 15, 362−365. For a unique approach to indoles via alkynes, see:
(j) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689−6690.
(k) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63,
7652−7662.
Rossi, E. Eur. J. Org. Chem. 2007, 517−525. (c) Hussain, M.; Tung, Đ.
̀
T.; Langer, P. Synlett 2009, 1822−1826. (d) Zheng, C.; Lu, Y. P.;
Zhang, J.; Chen, X.; Chai, Z.; Ma, W.; Zhao, G. Chem. −Eur. J. 2010,
16, 5853−5857. (e) Wang, X.-F.; Chen, J.-R.; Cao, Y.-J.; Cheng, H.-G.;
Xiao, W.-J. Org. Lett. 2010, 12, 1140−1143. (f) Masuda, K.; Ohmura,
T.; Suginome, M. Organometallics 2011, 30, 1322−1325. (g) Daly, S.;
Hayden, K.; Malik, I.; Porch, N.; Tang, H.; Rogelj, S.; Frolova, L.;
Lepthien, K.; Kornienko, A.; Magedov, I. V. Bioorg. Med. Chem. Lett.
2011, 21, 4720−4723. (h) Pirovano, V.; Abbiati, G.; Dell’Aqua, M.;
Facoetti, D.; Giordano, M.; Rossi, E. Synlett 2012, 23, 2913−2918.
(i) Pirovano, V.; Decataldo, L.; Rossi, E.; Vicente, R. Chem. Commun.
2013, 49, 3594−3596. (j) Tian, X.; Hofmann, N.; Melchiorre, P.
Angew. Chem., Int. Ed. 2014, 53, 2997−3000.
(15) For some selected methods, see: (a) Moskalev, N.;
Barbasiewicz, M.; Mąkosza, M. Tetrahedron 2004, 60, 347−358.
(b) Tsang, W. C. P.; Munday, R. H.; Brasche, G.; Zheng, N.;
Buchwald, S. L. J. Org. Chem. 2008, 73, 7603−7610. (c) Vara, Y.;
Aldaba, E.; Arrieta, A.; Pizarro, J. L.; Arriortua, M. I.; Cossío, F. P. Org.
Biomol. Chem. 2008, 6, 1763−1772. (d) Nakanishi, M.; Katayev, D.;
Besnard, C.; Kundig, E. P. Angew. Chem., Int. Ed. 2011, 50, 7438−
̈
7441. (e) Mahajan, J. P.; Suryawanshi, Y. R.; Mhaske, S. B. Org. Lett.
2012, 14, 5804−5807. (f) Zhang, X.; Zhang-Negrerie, D.; Deng, J.;
Du, Y.; Zhao, K. J. Org. Chem. 2013, 78, 12750−12759. (g) Abaev, V.
T.; Plieva, A. T.; Chalikidi, P. N.; Uchuskin, M. G.; Trushkov, I. V.;
Butin, A. V. Org. Lett. 2014, 16, 4150−4153.
(8) For select reviews on oxidative olefination reactions, see: (a) Jia,
C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633−639.
(b) Bras, J. L.; Muzart, J. Chem. Rev. 2011, 111, 1170−1214.
(c) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215−1292.
(d) Kozhushkov, S.; Ackermann, L. Chem. Sci. 2013, 4, 886−896.
(e) Shang, X.; Liu, Z.-Q. Chem. Soc. Rev. 2013, 42, 3253−3260. For
some selected synthesis of 2-alkenylindoles via C−H functionalization,
see: (f) Grimster, N. P.; Gauntlett, C.; Godfrey, C. R. A.; Gaunt, M. J.
Angew. Chem., Int. Ed. 2005, 44, 3125−3129. (g) Capito, E.; Brown, J.
M.; Ricci, A. Chem. Commun. 2005, 1854−1856. (h) Maehara, A.;
Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1159−1162.
(16) (a) Hegedus, L. S.; Allen, G. F.; Waterman, E. L. J. Am. Chem.
Soc. 1976, 98, 2674−2676. (b) Sakamoto, T.; Nagano, T.; Kondo, Y.;
Yamanaka, H. Synthesis 1990, 215−218. (c) Bernini, R.; Cacchi, S.;
Fabrizi, G.; Filisti, E.; Sferrazza, A. Synlett 2009, 1480−1484.
(d) Bernini, R.; Fabrizi, G.; Sferrazza, A.; Cacchi, S. Angew. Chem.,
Int. Ed. 2009, 48, 8078−8081. (e) Ji, X.; Huang, H.; Wu, W.; Li, X.;
Jiang, H. J. Org. Chem. 2013, 78, 11155−11162. (f) Jang, Y. H.; Youn,
S. W. Org. Lett. 2014, 16, 3720−3723. See also: (g) Alonso, F.;
Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079−3159.
(17) Cho, C. S.; Kim, J. U. Tetrahedron Lett. 2007, 48, 3775−3778.
(18) (a) Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116,
5969−5970. (b) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994,
116, 7901−7902.
́
(i) García-Rubia, A.; Arrayas, R. G.; Carretero, J. C. Angew. Chem., Int.
Ed. 2009, 48, 6511−6515. (j) Ueyama, T.; Mochida, S.; Fukutani, T.;
Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2011, 13, 706−708.
(k) Ackermann, L.; Wang, L.; Wolfram, R.; Lygin, A. V. Org. Lett.
2012, 14, 728−731. (l) Padala, K.; Jeganmohan, M. Org. Lett. 2012,
14, 1134−1137. (m) Lanke, V.; Prabhu, K. R. Org. Lett. 2013, 15,
2818−2821. (n) Li, B.; Ma, J.; Xie, W.; Song, H.; Xu, S.; Wang, B.
Chem. −Eur. J. 2013, 19, 11863−11868. (o) Zhang, L.-Q.; Yang, S.;
Huang, X.; You, J.; Song, F. Chem. Commun. 2013, 49, 8830−8832.
(p) Li, B.; Ma, J.; Xie, W.; Song, H.; Xu, S.; Wang, B. J. Org. Chem.
2013, 78, 9345−9353. (q) Sharma, S.; Han, S.; Kim, M.; Mishra, N.
K.; Park, J.; Shin, Y.; Ha, J.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Org.
Biomol. Chem. 2014, 12, 1703−1706. (r) Tang, C.-Y.; Tao, Y.; Wu, X.-
Y.; Sha, F. Adv. Synth. Catal. 2014, 356, 609−615.
(19) Danishefsky, S. J.; Kitahara, T. J. Am. Chem. Soc. 1974, 96,
7807−7808.
(20) For a comprehensive review on carbazoles and their synthesis,
see: (a) Schmidt, A. W.; Reddy, K. R.; Knolker, H.-J. Chem. Rev. 2012,
̈
112, 3193−3328 and references cited therein. See also: (b) Gao, H.;
Xu, Q.-L.; Yousufuddin, M.; Ess, D. H.; Kurti, L. Angew. Chem. Int. Ed.
̈
2014, 53, 2701−2705.
(9) For other different approaches, see: (a) Fayol, A.; Fang, Y.-Q.;
Lautens, M. Org. Lett. 2006, 8, 4203−4206. (b) Rossi, E.; Abbiati, G.;
Canevari, V.; Celentano, G.; Magri, E. Synthesis 2006, 299−304.
(c) Zhao, Z.; Jaworski, A.; Piel, I.; Snieckus, V. Org. Lett. 2008, 10,
́ ́
2617−2620. (d) Barluenga, J.; Jimenez-Aquino, A.; Aznar, F.; Valdes,
C. J. Am. Chem. Soc. 2009, 131, 4031−4041. (e) Tobisu, M.; Fujihara,
H.; Koh, K.; Chatani, N. J. Org. Chem. 2010, 75, 4841−4847.
(f) Wang, Y.; Liu, L.; Zhang, L. Chem. Sci. 2013, 4, 739−746. (g) Das,
B.; Kundu, P.; Choudhury, C. Org. Biomol. Chem. 2014, 12, 741−748.
(10) For some reviews on α-arylation of activated C−H bonds, see:
(a) Bellina, F.; Rossi, R. Chem. Rev. 2009, 109, 1082−1146.
(b) Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed. 2010,
49, 676−707. (c) Sivanandan, S. T.; Shaji, A.; Ibnusaud, I.; Johansson
Seechurn, C. C. C.; Colacot, T. J. Eur. J. Org. Chem. 2015, 38−49.
(11) Kale, A. P.; Pawar, G. G.; Kapur, M. Org. Lett. 2012, 14, 1808−
1811.
(12) Su, W. P.; Raders, S.; Verkade, J. G.; Liao, X. B.; Hartwig, J. F.
Angew. Chem., Int. Ed. 2006, 45, 5852−5855.
(13) (a) Kuwajima, I.; Urabe, H. J. Am. Chem. Soc. 1982, 104, 6831−
6833. (b) Kuwajima, I.; Nakamura, E. Acc. Chem. Res. 1985, 18, 181−
187.
(14) (a) Chen, C.-yi.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, P.
J.; Reider, T. R. J. Org. Chem. 1997, 62, 2676−2677. (b) Sole,
́
D.;
Vallverdu, L.; Peidro, E.; Bonjoch, J. Chem. Commun. 2001, 1888−
́
́
D
Org. Lett. XXXX, XXX, XXX−XXX