Organic Letters
Letter
W. J. J. Am. Chem. Soc. 2010, 132, 3664−3665. (c)) Qian, H.; Yu, X.;
Zhang, J.; Sun, J. J. Am. Chem. Soc. 2013, 135, 18020. (d) Mbofana, C.
T.; Miller, S. J. J. Am. Chem. Soc. 2014, 136, 3285. (e) Jiang, Y.;
Diagne, A. B.; Thomson, R. J.; Schaus, S. E. J. Am. Chem. Soc. 2017,
139, 1998. (f) Poulsen, P. H.; Li, Y.; Lauridsen, V. H.; Jørgensen, D.
K. B.; Palazzo, T. A.; Meazza, M.; Jørgensen, K. A. Angew. Chem., Int.
Ed. 2018, 57, 10661.
(8) (a) For selected examples of the synthesis of chiral
tetrasubstituted allenes via metal catalysis, see: Partridge, B. M.;
Chausset-Boissarie, L.; Burns, M.; Pulis, A. P.; Aggarwal, V. K. Angew.
(g) Zhang, M.-Z.; Jia, C.-Y.; Gu, Y.-C.; Mulholland, N.; Turner, S.;
Beattie, D.; Zhang, W.-H.; Yang, G.-F.; Clough, J. Eur. J. Med. Chem.
2017, 126, 669.
(16) CCDC 2010785 (3z) and CCDC 2010790 (5d) contain the
supplementary crystallographic data for this paper. These data can be
obtained free of charge from The Cambridge Crystallographic Data
(17) (a) Kumar, D.; Sharma, P.; Singh, H.; Nepali, K.; Gupta, G. K.;
Jain, S. K.; Ntie-Kang, F. RSC Adv. 2017, 7, 36977. (b) Robb, M. J.;
Kim, T.; Halmes, A. J.; White, S. R.; Sottos, N. R.; Moore, J. S. J. Am.
Chem. Soc. 2016, 138, 12328. (c) Abdissa, N.; Pan, F.; Gruhonjic, A.;
Chem., Int. Ed. 2012, 51, 11795. (b) Scheipers, I.; Muck-Lichtenfeld,
̈
̈
Grafenstein, J.; Fitzpatrick, P. A.; Landberg, G.; Rissanen, K.;
C.; Studer, A. Angew. Chem., Int. Ed. 2019, 58, 6545. (c) Zheng, W.-
F.; Zhang, W.; Huang, C.; Wu, P.; Qian, H.; Wang, L.; Guo, Y.-L.;
Ma, S. Nat. Catal. 2019, 2, 997. (d) Aparece, M. D.; Hu, W.; Morken,
J. P. ACS Catal. 2019, 9, 11381. (e) For organocatalytic methods,
see: Hashimoto, T.; Sakata, K.; Tamakuni, F.; Dutton, M. J.;
Maruoka, K. Nat. Chem. 2013, 5, 240. (f) Tap, A.; Blond, A.;
Wakchaure, V. N.; List, B. Angew. Chem., Int. Ed. 2016, 55, 8962.
(g) Qian, D.; Wu, L.; Lin, Z.; Sun, J. Nat. Commun. 2017, 8, 567.
(h) Chen, M.; Qian, D.; Sun, J. Org. Lett. 2019, 21, 8127. (i) Zhang,
P.; Huang, Q.; Cheng, Y.; Li, R.; Li, P.; Li, W. Org. Lett. 2019, 21, 503.
(j) Yang, J.; Wang, Z.; He, Z.; Li, G.; Hong, L.; Sun, W.; Wang, R.
Angew. Chem., Int. Ed. 2020, 59, 642.
́
Yenesew, A.; Erdelyi, M. J. Nat. Prod. 2016, 79, 2181.
(9) (a) For selected recent reports of the synthesis of
tetrasubstituted allenes via C−H functionalization reaction, see: Wu,
S.; Huang, X.; Wu, W.; Li, P.; Fu, C.; Ma, S. Nat. Commun. 2015, 6,
7946. (b) Lu, Q.; Greßies, S.; Klauck, F. J. R.; Glorius, F. Angew.
Chem., Int. Ed. 2017, 56, 6660. (c) Sen, M.; Dahiya, P.; Premkumar, J.
R.; Sundararaju, B. Org. Lett. 2017, 19, 3699. (d) Wu, S.; Huang, X.;
Fu, C.; Ma, S. Org. Chem. Front. 2017, 4, 2002.
(10) Huang, Z.; Lumb, J.-P. ACS Catal. 2019, 9, 521.
(11) (a) Huang, L.-J.; Weng, J.; Wang, S. Lu. G.; Lu, G. Adv. Synth.
Catal. 2015, 357, 993. (b) Weng, J.; Wang, S.; Huang, L.-J.; Luo, Z.-
Y.; Lu, G. Chem. Commun. 2015, 51, 10170. (c) Huang, W.-J.; Chen,
Q.; Lin, N.; Long, X.-W.; Pan, W.-G.; Xiong, Y.-S.; Weng, J.; Lu, G.
Org. Chem. Front. 2017, 4, 472. (d) Zhu, W.-R.; Chen, Q.; Lin, N.;
Chen, K.-B.; Zhang, Z.-W.; Fang, G.; Weng, J.; Lu, G. Org. Chem.
Front. 2018, 5, 1375. (e) Zhu, W.-R.; Liu, K.; Weng, J.; Huang, W.-H.;
Huang, W.-J.; Chen, Q.; Lin, N.; Lu, G. Org. Lett. 2020, 22, 5014.
(12) During the preparation of the manuscript, Sun and co-workers
reported an organocatalytic enantioselective synthesis of tetrasub-
stituted allenes from 2-indolyl propargylic alcohols and nucleophiles:
(13) (a) For selected reviews, see: Akiyama, T. Chem. Rev. 2007,
107, 5744. (b) Terada, M. Chem. Commun. 2008, 4097. (c) Parmar,
D.; Sugiono, E.; Raja, S.; Rueping, M. Chem. Rev. 2014, 114, 9047.
(d) James, T.; van Gemmeren, M.; List, B. Chem. Rev. 2015, 115,
9388. For selected examples, see: (e) Uraguchi, D.; Terada, M. J. Am.
Chem. Soc. 2004, 126, 5356. (f) Akiyama, T.; Itoh, J.; Yokota, K.;
Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566. (g) Yue, C.; Na, F.;
Fang, X.; Cao, Y.; Antilla, J. C. Angew. Chem., Int. Ed. 2018, 57, 11004.
(h) Jiang, F.; Chen, K.-W.; Wu, P.; Zhang, Y.-C.; Jiao, Y.; Shi, F.
Angew. Chem., Int. Ed. 2019, 58, 15104. (i) Meng, S.-S.; Yu, P.; Yu, Y.-
Z.; Liang, Y.; Houk, K. N.; Zheng, W.-H. J. Am. Chem. Soc. 2020, 142,
8506.
(14) (a) For selected examples of the synthesis of allenes bearing
indole moieties, see: Chen, B.; Fan, W.; Chai, G.; Ma, S. Org. Lett.
2012, 14, 3616. (b) Uruvakili, A.; Kumara Swamy, K. C. Org. Biomol.
Chem. 2019, 17, 3275.
(15) (a) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875.
(b) Inman, M.; Moody, C. J. Chem. Sci. 2013, 4, 29. (c) Gurkan-Alp,
A. S.; Mumcuoglu, M.; Andac, C. A.; Dayanc, E.; Cetin-Atalay, R.;
Buyukbingol, E. Eur. J. Med. Chem. 2012, 58, 346. (d) Zhuang, S.-H.;
Lin, Y.-C.; Chou, L.-C.; Hsu, M.-H.; Lin, H.-Y.; Huang, C.-H.; Lien,
J.-C.; Kuo, S.-C.; Huang, L.-J. Eur. J. Med. Chem. 2013, 66, 466.
(e) Hwang, D.-J.; Wang, J.; Li, W.; Miller, D. D. ACS Med. Chem. Lett.
2015, 6, 993. (f) Wang, J.-J.; Shen, Y.-K.; Hu, W.-P.; Hsieh, M.-C.;
Lin, F.-L.; Hsu, M.-K.; Hsu, M.-H. J. Med. Chem. 2006, 49, 1442.
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