COMMUNICATIONS
7
166; Ni: l) R. M. Stolley, H. A. Duong, D. R. Thomas,
Chen, C. Wang, J. Am. Chem. Soc. 2013, 135, 1264–
1267; c) R. He, X. Jin, H. Chen, Z.-T. Huang, Q.-Y.
Zheng, C. Wang, J. Am. Chem. Soc. 2014, 136, 6558–
6561; d) R. He, Z.-T. Huang, Q.-Y. Zheng, C. Wang,
Angew. Chem. 2014, 126, 5050–5053; Angew. Chem.
Int. Ed. 2014, 53, 4950–4953; e) B. Zhou, Y. Hu, C.
Wang, Angew. Chem. 2015, 127, 13863–13867; Angew.
Chem. Int. Ed. 2015, 54, 13659–13663. For contributions
from other groups: f) Y. Kuninobu, Y. Nishina, T. Take-
uchi, K. Takai, Angew. Chem. 2007, 119, 6638–6640;
Angew. Chem. Int. Ed. 2007, 46, 6518–6520; g) W. Liu,
D. Zell, M. John, L. Ackermann, Angew. Chem. 2015,
J. Louie, J. Am. Chem. Soc. 2012, 134, 15154–15162; Ir:
m) G. Onodera, Y. Shimizu, J.-N. Kimura, J. Kobayashi,
Y. Ebihara, K. Kondo, K. Sakata, R. Takeuchi, J. Am.
Chem. Soc. 2012, 134, 10515–10531; Ti: n) D. Suzuki, Y.
Nobe, Y. Watai, R. Tanaka, Y. Takayama, F. Sato, H.
Urabe, J. Am. Chem. Soc. 2005, 127, 7474–7479; Au:
o) S. N. Karad, R. S. Liu, Angew. Chem. 2014, 126,
9
218–9222; Angew. Chem. Int. Ed. 2014, 53, 9072–9076.
For selected examples of [2+2+1] cyclizations, see:
p) W. He, C. Li, L. Zhang, J. Am. Chem. Soc. 2011,
1
1
Chem. Eur. J. 2014, 20, 8551–8555. For alkyne insertion
to C-CN bond: s) Y. Minami, H. Yoshiyasu, Y. Nakao,
T. Hiyama, Angew. Chem. 2013, 125, 917–921; Angew.
Chem. Int. Ed. 2013, 52, 883–887. For nucleophilic addi-
tion of terminal alkynes to nitriles: t) B. M. Trost, B.
Biannic, Org. Lett. 2015, 17, 1433–1436; u) S. Yang, X.
Zhu, S. Zhou, S. Wang, Z. Feng, Y. Wei, H. Miao, L.
Guo, F. Wang, G. Zhang, X. Gu, X. Mu, Sci. China
Chem. 2014, 57, 1090–1097.
33, 8482–8485; q) Y. Xiao, L. Zhang, Org. Lett. 2012,
4, 4662–4665; r) L. Hong, Y. Shao, L. Zhang, X. Zhou,
1
4
27, 4165–4169; Angew. Chem. Int. Ed. 2015, 54, 4092–
096; h) L. Shi, X. Zhong, H. She, Z. Lei, F. Li, Chem.
Commun. 2015, 51, 7136–7139; i) W. Liu, J. Bang, Y.
Zhang, L. Ackermann, Angew. Chem. 2015, 127,
1
4343–14346; Angew. Chem. Int. Ed. 2015, 54, 14137–
1
4140.
[
9] For more details, see the Supporting Information.
[
10] For the reason why the ortho-H-incorporation in the
second equation was lower than that in the first one,
see the Supporting Information.
[
[
4] J. Q. Yu, Z.-J. Shi, C–H Activation, Springer, Berlin,
[
11] E. M. Simmons, J. F. Hartwig, Angew. Chem. 2012, 124,
2
010.
3
120–3126; Angew. Chem. Int. Ed. 2012, 51, 3066–3072.
5] a) F. Kakiuchi, M. Sonoda, T. Tsujimoto, N. Chatani, S.
Murai, Chem. Lett. 1999, 1083–1084; b) W. Li, Z. Xu, P.
Sun, X. Jiang, M. Fang, Org. Lett. 2011, 13, 1286–1289;
c) J.-C. Wan, J.-M. Huang, Y.-H. Jhan, J.-C. Hsieh, Org.
Lett. 2013, 15, 2742–2745; d) W. Li, P. Sun, J. Org.
Chem. 2012, 77, 8362–8366; e) B. Du, X. Jiang, P. Sun,
J. Org. Chem. 2013, 78, 2786–2791; f) M. C. Reddy, M.
Jeganmohan, Chem. Commun. 2015, 51, 10738–10741.
For selected meta-CÀH activation using cyano tem-
[
12] a) L. S. Liebeskind, J. R. Gasdaska, J. S. McCallum, S. J.
Tremont, J. Org. Chem. 1989, 54, 669–677; b) N. P. Rob-
inson, L. Main, B. K. Nicholson, J. Organomet. Chem.
1
989, 364, C37–C39; c) R. C. Cambie, M. R. Metzler,
P. S. Rutledge, P. D. Woodgate, J. Organomet. Chem.
990, 398, C22–C24; d) W. J. Grigsby, L. Main, B. K.
1
Nicholson, Organometallics 1993, 12, 397–407; e) A.
Suꢂrez, F. Faraldo, J. M. Vila, H. Adams, A. Fernꢂndez,
M. Lꢅpez-Torres, J. J. Fernꢂndez, J. Organomet. Chem.
plates: g) D. Leow, G. Li, T.-S. Mei, J.-Q. Yu, Nature
2
002, 656, 270–273.
2
012, 486, 518–522; h) R.-Y. Tang, G. Li, J.-Q. Yu,
[
13] a) L. Ackermann, Chem. Rev. 2011, 111, 1315–1345;
b) G. Shi, Y. Zhang, Adv. Synth. Catal. 2014, 356, 1419–
Nature 2014, 507, 215–220. For transformations of ni-
triles to amides: i) M. C. Reddy, R. Manikandan, M. Je-
ganmohan, Chem. Commun. 2013, 49, 6060–6062; j) P.
Lu, C. Feng, T.-P. Loh, Acta Chim. Sinica 2015, 73,
1
442.
[
[
[
14] A. A. Reid, J. T. Sharp, H. R. Sood, P. B. Thorgood, J.
Chem. Soc. Perkin Trans. 1 1973, 2543–2551.
15] D. C. Remy, W. A. Van Saun Jr, E. L. Engelhardt, J.
Med. Chem. 1975, 18, 142–148.
16] D. Scholz, H. Schmidt, E. E. Prieschl, P. R. Csonga, W.
Scheirer, V. Weber, A. Lembachner, G. Seidl, G.
Werner, P. Mayer, T. Baumruker, J. Med. Chem. 1998,
41, 1050–1059.
1
315–1319.
6] a) D. G. Yu, M. Suri, F. Glorius, J. Am. Chem. Soc.
013, 135, 8802–8805; b) Z. Shi, D. C. Koester, M.
Boultadakis-Arapinis, F. Glorius, J. Am. Chem. Soc.
013, 135, 12204–12207; c) S. Sueki, Y. Guo, M. Kanai,
[
2
2
Y. Kuninobu, Angew. Chem. 2013, 125, 12095–12099;
Angew. Chem. Int. Ed. 2013, 52, 11879–11883.
[
[
7] a) F. C. Schaefer, G. A. Peters, J. Org. Chem. 1961, 26,
[17] G. C. Bellinger, W. E. Campbell, R. G. F. Giles, J. D.
Tobias, J. Chem. Soc. Perkin Trans. 1 1982, 2819–2825.
[18] S. A. Shahzad, C. Venin, T. Wirth, Eur. J. Org. Chem.
2010, 2010, 3465–3472.
4
6
12–418; b) R. Roger, D. G. Neilson, Chem. Rev. 1961,
1, 179–211; c) V. K. Yadav, K. G. Babu, Eur. J. Org.
Chem. 2005, 452–456.
8] For a review: a) C. Wang, Synlett 2013, 24, 1606–1613.
For contributions from our group: b) B. Zhou, H.
[19] X. Han, H. Wu, C. Dong, P. Tien, W. Xie, S. Wu, H.-B.
Zhou, RSC Adv. 2015, 5, 10005–10013.
Adv. Synth. Catal. 0000, 000, 0 – 0
7
ꢁ 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
ÞÞ
These are not the final page numbers!