Journal of the American Chemical Society
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Figure 1. Comparison of the energy profiles (ꢁG in kcal mol−1) of path a (black) and path b (blue) for the decarbonylation of indole 1a
(k) Dermenci, A.; Coe, J. W.; Dong, G. Org. Chem. Front. 2014, 1, 567.
AUTHOR INFORMATION
(l) Liu, H.; Feng, M.; Jiang, X. Chem. - Asian J. 2014, 9, 3360. (m) Souilꢀ
lart, L.; Cramer, N. Chem. Rev. 2015, 115, 9410. (n) Kondo, T. Eur. J.
Org. Chem. 2016, 2016, 1232. (o) Murakami, M.; Ishida, N. J. Am. Chem.
Soc. 2016, 138, 13759. (o) Somerville, R. J.; Martin, R. Angew. Chem. Int.
Ed. 2017, 56, 6708.
(4) Books on C−C bond activation: (a) J. W. Grate, G. C. Frye in Sensors
Update, Vol. 2 (Eds.: H. Baltes, W. Gçpel, J. Hesse), WileyꢀVCH, Weinꢀ
heim, 1996. (b) Dong, G., Ed. C−C bond activation; Springer Verlag:
Berlin/Heidelberg, 2014. (c) Cleavage of Carbon−Carbon Single Bonds
by Transition Metals; Murakami, M.; Chatani, N., Ed.; John Wiley &
Sons Ltd.: Chichester, U.K., 2016.
Corresponding Author
*haow@nwu.edu.cn
*xupf@lzu.edu.cn
Author Contributions
§
These authors contributed equally to this work.
Notes
The authors declare no competing financial interests.
(5) Daugulis, O.; Brookhart, M. Organometallics 2004, 23, 527.
(6) Lei, Z.ꢀQ.; Li, H.; Li, Y.; Zhang, X.ꢀS.; Chen, K.; Wang, X.; Sun, J.;
Shi, Z.ꢀJ. Angew. Chem., Int. Ed. 2012, 51, 2690.
ACKNOWLEDGMENT
(7) (a) Zeng, R.; Dong, G. J. Am. Chem. Soc. 2015, 137, 1408. (b) Dennis,
J. M.; Compagner, C. T.; Dorn, S. K.; Johnson, J. B. Org. Lett. 2016, 18,
3334. (c) Xia, Y.; Lu, G.; Liu, P.; Dong, G. Nature 2016, 539, 546. (d)
Xia, Y.; Wang, J.; Dong, G. Angew. Chem., Int. Ed. 2017, 56, 2376.
(8) Selected reviews (a) Li, B.ꢀJ.; Yu, D.ꢀG.; Sun, C.ꢀL.; Shi, Z.ꢀJ. Chem.
Eur. J. 2011, 17, 1728. (b) Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.;
Zhang, N.; Resmerita, A.ꢀM.; Garg, N. K.; Percec, V. Chem. Rev. 2011,
111, 1346. (c) Yu, D.ꢀG.; Li, B.ꢀJ.; Shi, Z.ꢀJ. Acc. Chem. Res. 2010, 43,
1486. (d) Mesganaw, T.; Garg, N. K. Org. Process Res. Dev. 2013, 17, 29.
(d) Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299. (e)
Ouyang, K.; Hao, W.; Zhang, W.ꢀX.; Xi, Z. Chem. Rev. 2015, 115, 12045.
(f) Tollefson, E. J.; Hanna, L. E.; Jarvo, E. R. Acc. Chem. Res. 2015, 48,
2344. (g) Tobisu, M.; Chatani, N. Acc. Chem. Res. 2015, 48, 1717. (h)
Iwasaki, T.; Kambe, N. Top Curr. Chem. 2016, 374, 66.
(9) Morioka, T.; Nishizawa, A.; Furukawa, T.; Tobisu, M.; Chatani, N. J.
Am. Chem. Soc. 2017, 139, 1416.
(10) See the Supporting Information (SI) for details.
(11) (a) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc.
1999, 121, 8645. (b) Obenhuber, A.; Ruhland, K.; Hoffmann, S. D. Or-
ganometallics 2008, 27, 3482.
(12) Nickelꢀcatalyzed reactions of strained ketones involving the oxidative
addition into C−C bond: (a) Murakami, M.; Ashida, S.; Matsuda, T. J. Am.
Chem. Soc. 2005, 127, 6932. (b) Murakami, M.; Ashida, S.; Matsuda, T.
Tetrahedron 2006, 62, 7540. (c) Murakami, M.; Ishida, N.; Miura, T.
Chem. Commun. 2006, 643. (d) Auvinet, A.ꢀL.; Harrity, J. P. A. Angew.
Chem., Int. Ed. 2011, 50, 2769. (e) Liu, L.; Ishida, N.; Murakami, M.
Angew. Chem., Int. Ed. 2012, 51, 2485. (f) Kumar, P.; Louie, J. Org. Lett.
2012, 14, 2026. (g) Kumar, P.; Zhang, K.; Louie, J. Angew. Chem., Int.
Ed. 2012, 51, 8602. (h) Thakur, A.; Facer, M. E.; Louie, J. Angew. Chem.,
Int. Ed. 2013, 52, 12161. (i) JuliáꢀHernández, F.; Ziadi, A.; Nishimura, A.;
Martin, R. Angew. Chem., Int. Ed. 2015, 54, 9537.
We are grateful to the financial support from the National Natural
Science Foundation of China (NSFC 21502149 and 21632003)
and Scientific Research Program Funded by Shaanxi Provincial
Education Department (Program No. 17JS129 and 15JK1749).
We thank Prof. ZhiꢀXiang Yu and Dr. Uwe Schneider for insightꢀ
ful discussions.
REFERENCES
(1) (a) Murphy, A. R.; Fréchet, J. M. J. Chem. Rev. 2007, 107, 1066. (b)
Hughes, R. A.; Moody, C. J. Angew. Chem. Int. Ed. 2007, 46, 7930. (c)
Dolle, R. E.; Bourdonnec, B. L.; Worm, K.; Morales, G. A.; Thomas, C. J.;
Zhang, W. J. Comb. Chem. 2010, 12, 765. (d) Young, I. S.; Thornton, P.
D.; Thompson, A. Nat. Prod. Rep. 2010, 27, 1801. (e) Wang, C.; Dong, H.;
Hu, W.; Liu, Y.; Zhu, D. Chem. Rev. 2012, 112, 2208.
(2) (a) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540. (b) Muraꢀ
kami, M.; Amii, H.; Shigeto, K.; Ito, Y. J. Am. Chem. Soc. 1996, 118,
8285. (c) Murakami, M.; Itahashi, T.; Amii, H.; Takahashi, K.; Ito, Y. J.
Am. Chem. Soc. 1998, 120, 9949. (d) Masuda, Y.; Hasegawa, M.; Yamaꢀ
shita, M.; Nozaki, K.; Ishida, N.; Murakami, M. J. Am. Chem. Soc. 2013,
135, 7142.(e) Kaneda, K.; Azuma, H.; Wayaku, M.; Tehanishi, S. Chem.
Lett.1974, 3, 215. (f) Dermenci, A.; Whittaker, R.; Dong, G. Org. Lett.
2013, 15, 2242. (g) Whittaker, R.; Dong, G. Org. Lett. 2015, 17, 5504. (h)
Dermenci, A.; Whittaker, R. E.; Gao, Y.; Cruz, F. A.; Yu, Z.ꢀX.; Dong, G.
Chem. Sci. 2015, 6, 3201.
(3) Reviews/highlights on C−C bond activation: (a) Crabtree, R. H. Chem.
Rev. 1985, 85, 245. (b) Murakami, M.; Ito, Y. Top. Organomet. Chem.
1999, 3, 97. (c) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed.
1999, 38, 870. (d) Baciocchi, E.; Bietti, M.; Lanzalunga, O. Acc. Chem.
Res. 2000, 33, 243. (e) Jun, C.ꢀH. Chem. Soc. Rev. 2004, 33, 610. (f) Tu,
W.; Floreancig, P. E. Org. Lett. 2007, 9, 2389. (g) Park, Y. J.; Park, J.ꢀW.;
Jun, C.ꢀH. Acc. Chem. Res. 2008, 41, 222. (h) Murakami, M.; Matsuda, T.
Chem. Commun. 2011, 47, 1100. (i) Ruhland, K. Eur. J. Org. Chem. 2012,
2012, 2683. (j) Chen, F.; Wang, T.; Jiao, N. Chem. Rev. 2014, 114, 8613.
(13) Ackermann, L.; Lygin, A. V. Org. Lett. 2011, 13, 3332.
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