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ChemComm
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COMMUNICATION
Journal Name
74−100; (e) G. Rouquet and N. Chatani, Angew. Chem. Int.
Ed. 2013, 52, 11726−11743; (f) P. B. Arockiam, C. Bruneau
and P. H. Dixneuf, Chem. Rev. 2012, 112, 5879−5918; (g) L.
Ackermann, Chem. Rev. 2011, 111, 1315-1345; (h) T. Satoh
and M. Miura, Chem. Eur. J. 2010, 16, 11212−11222; (i) R.
Giri, B.–F. Shi, K.–M. Engle, N. Maugel and J.–Q. Yu, Chem.
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functionalizations, see: (a) G. Cera and L. Ackermann, Top.
Curr. Chem. 2016, 374, 57; (b) E. NakDamOIu: 1r0a.1a0n3d9/CN7.CYCo0s3h3i7k6aAi
J., Org. Chem. 2010, 75, 6061-6067. For iron-catalyzed C–H
functionalizations through triazole assistance, see: (c) G.
Cera, T. Haven and L. Ackermann, Chem. -Eur. J. 2017, 23
,
Soc. Rev. 2009,
3
, 3242−3272; (j) R. G. Bergman, Nature
3577-3582; (d) G. Cera, T. Haven and L. Ackermann, Angew.
Chem. Int. Ed. 2016, 55, 1484-1488; (e) K. Graczyk, T. Haven
and L. Ackermann, Chem. Eur. J. 2015, 21, 8812-8815; (f) Q.
Qu, H. H. Al Mamari, K. Graczyk, E. Diers and L. Ackermann,
Angew. Chem. Int. Ed. 2014, 53, 3868-3871.
2007, 446, 391−393 and references cited therein.
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For representive recent reviews see: (a) L. Ackermann, Acc.
Chem. Res. 2014, 47, 281-295; (b) G. Song, F. Wang and X. Li,
Chem. Soc. Rev. 2012, 41, 3651-3678; (c) T. Satoh and M.
Miura, Chem.-Eur. J. 2010, 16
examples of isoquinolone
,
11212-11122. Selected 10 For
syntheses via C–H
a recent elegant example of iron-catalyzed C–H
hydroarylation/annulation strategy see: T. Jia, C. Zhao, R. He,
H. Chen and C. Wang, Angew. Chem. Int. Ed. 2016, 55, 5268-
5271.
functionalizations with 4d and 5d metals: for rhodium, see:
(d) N. J. Webb, S. P. Madsen and S. A. Raw, Org. Lett. 2014,
16, 4716-4721; (e) H. Wang, C. Grohmann, C. Nimphius and 11 For a recent study on quinolone assistance: T. Matsubara, L.
F. Glorius, J. Am. Chem. Soc. 2012, 134, 19592-19595; (f) T. K.
Hyster and T. Rovis, J. Am. Chem. Soc. 2010, 132, 10565- 12 R. M. Beesley, C. K. Ingold and J. F. Thorpe, J. Chem. Soc.,
10569; (g) N. Guimond, C. Gouliaras and K. Fagnou, J. Am. Trans., 1915, 107, 1080-1106.
Ilies and E. Nakamura, Chem. Asian J. 2016, 11, 380-384.
Chem. Soc. 2010, 132, 5858-5859. For ruthenium, see: (h) B. 13 For detailed information, see the Supporting Information.
Li, H. Feng, S. Xu and B. Wang, Chem. Eur. J. 2011, 17, 12573- 14 Y. Sun, H. Tang, K. Chen, L. Hu, J. Yao, S. Shaik and H. Chen, J.
12577; (i) L. Ackermann, A. V. Lygin and N. Hoffmann,
Angew. Chem. Int. Ed. 2011, 123 6503-6506; (j) L. 15 For the traceless removal of the reusable TAM group, see
references [9c-f].
Am. Chem. Soc. 2016, 138, 3715-3730.
,
Ackermann and S. Fenner, Org. Lett. 2011, 13, 6548-6551.
For palladium, see: (k) X. Peng, W. Wang, C. Jiang, D. Sun, Z.
Xu and C.–H. Tung, Org. Lett. 2014, 16, 5354-5357. For
rhenium see: (l) Q. Tang, D. Xia, X. Jin, Q. Zhang, X. -Q. Sun
and C. Wang, J. Am. Chem. Soc. 2013, 135, 4628-4631.
Selected examples of isoquinolone syntheses via bidentate-
assisted C–H functionalizations with 3d metals: for nickel
see: (a) H. Shiota, Y. Ano, Y. Aihara, Y. Fukumoto and N.
Chatani, J. Am. Chem. Soc. 2011, 133, 14952-14955; for
cobalt see: (b) X.-Q Hao, C. Du, X. Zhu, P.-X. Li, J.-H. Zhang, J.-
L. Niu and M.-P. Song, Org. Lett. 2016, 18, 3610-3613; (c) R.
Mei, H. Wang, S. Warratz, S. A. Macgregor and L. Ackermann,
Chem. -Eur. J. 2016, 22, 6759-6753; (d) G. Sivakumar, A.
Vijeta and M. Jeganmohan, Chem. -Eur. J. 2016, 22, 5899-
5903; (e) L: Grigorjeva and O. Daugulis, Angew. Chem. Int.
Ed. 2014, 53, 10209−10212; (f) L: Grigorjeva and O. Daugulis,
Org. Lett. 2014, 16, 4684-4687.
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6
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A review: O. Daugulis, J. Roane and L. D. Tran, Acc. Chem.
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For examples of triazolyl-amine (TAM) assisted C–H
functionalizations with 4d transition metals, see: (a) D.
Santrac, S. Cella, W. Wang and L. Ackermann, Eur. J. Org.
Chem. 2016, 32, 5429-5436; (b) X. Ye, Y. Zhang, Y. He and X.
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Zhu, S. Li, C. Ding and D. Ding, Org. Biomol. Chem. 2015, 13
,
5444–5450 (d) H. H. Al Mamari, E. Diers and L. Ackermann,
Chem. -Eur. J. 2014, 20, 9739-9743. For examples of 1,2,3
triazole-assisted-C–H functionalizations see: (e) A. Irastorza,
J. M. Aizpurua and A. Correa, Org. Lett. 2016, 18, 1080-1083;
(f) X. Ye and X. Shi, Org. Lett. 2014, 16, 4448-4451; (g) X. Ye,
Z. He, T. Ahmed and X. Shi, Chem. Sci. 2013,
4, 3712-3716;
(h) L. Ackermann, R. Born and R. Vicente, Chem. Sus. Chem.
2009,
2, 546-549; (i) L. Ackermann, R. Vicente and A.
Althammer, Org. Lett. 2008, 10, 2299-2302.
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For reviews on iron catalysis, see: (a) O. M. Kuzmina, A. K.
Steib, A. Moyeux, G. Cahiez and P. Knochel, Synthesis 2015,
47, 1696-1705; (b) I. Bauer and H.-J. Knölker, Chem. Rev.,
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and C. Bolm, Chem. Soc. Rev. 2008, 37, 1108-117.
4 | J. Name., 2012, 00, 1-3
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