Directed C-H Functionalization Catalyzed by Manganese or Chromium

Chapter1

1 Metal-Catalyzed Cross-Coupling Reactions and More; de Meijere, A., Bräse, S., Oestreich, M., Eds.; Wiley-VCH: Weinheim, 2014.

2 Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529−531.

3 (a) Handbook of C−H Transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, 2005. (b) Topics in Current Chemistry: C−H Activation; Yu, J.-Q., Shi, Z., Eds.; Springer-Verlag: Berlin, 2010. (c) Topics in Organometallic Chemistry: C−H Bond Activation and Catalytic Functionalization; Dixneuf, P. H., Doucet, H., Eds.; Springer International Publishing, 2016.

4 Vesborg, P. C. K.; Jaramillo, T. F. RSC Adv. 2012, 2, 7933–7947.

5 Gandeepan, P.; Müller, T.; Zell, D.; Cera, G.; Warratz, S.; Ackermann, L. Chem. Rev., DOI: 10.1021/acs.chemrev.8b00507.

6 (a) Emsley, J. Manganese. In Nature’s Building Blocks: An A−Z. Guide to the Elements; Oxford University Press: Oxford, 2001; pp 249−253. (b) Ullmann’s Encyclopedia of Industrial Chemistry, 6th ed.; Wiley- VCH: Weinheim, 2003; Vol. 20, p 497.

7 For reviews on manganese-catalyzed C–H functionalization, see: (a) Wang, C. Synlett 2013, 24, 1606–1613. (b) Liu, W.; Ackermann, L. ACS Catal. 2016, 6, 3743–3752. (c) Valyaev, D. A.; Lavigne, G.; Lugan, N. Coord. Chem. Rev. 2016, 308, 191–235. (d) Carney, J. R.; Dillon, B. R.; Thomas, S. P. Eur. J. Org. Chem. 2016, 2016, 3912–3929. (e) Hu, Y.; Zhou, B.; Wang, C. Acc. Chem. Res. 2018, 51, 816–827. (f) Cano, R.; Mackey, K.; McGlacken, G. P. Catal. Sci. Technol. 2018, 8, 1251–1266.

8 (a) Liu, W.; Cera, G.; Oliveira, J. C. A.; Shen, Z.; Ackermann, L. Chem. - Eur. J. 2017, 23, 11524–11528. (b) Zhu, C.; Oliveira, J. C. A.; Shen, Z.; Huang, H.; Ackermann, L. ACS Catal. 2018, 8, 4402–4407.

9 Egorova, K. S.; Ananikov, V. P. Organometallics 2017, 36, 4071–4090.

10 Zeng, X.; Cong, X. Org. Chem. Front. 2015, 2, 69–72.

11 (a) Knochel, P. et al. Org. Lett. 2014, 16, 5208–5211. (b) Li, Y.; Deng, G.; Zeng, X. Organometallics 2016, 35, 747–750. (c) Yan, J.; Yoshikai, N. Org. Chem. Front. 2017, 4, 1972–1975. (d) Yoshikai, N. et al. Org. Lett. 2017, 19, 6630–6633. (e) Zeng, X. et al. Chem. Commun. 2018, 54, 9325–9328. (f) Liu, P.; Chen, C.; Cong, X.; Tang, J.; Zeng, X. Nature Communications, DOI: 10.1038/s41467-018-07069-1.

Chapter2

1 Shang, R.; Ilies, L.; Nakamura, E. Chem. Rev. 2017, 117, 9086–9139.

2 (a) Barreiro, E. J.; Kümmerle, A. E.; Fraga, C. A. M. Chem. Rev. 2011, 111, 5215– 5246. (b) Schönherr, H.; Cernak, T. Angew. Chem. Int. Ed. 2013, 52, 12256–12267.

3 (a) Yan, G.; Borah, A. J.; Wang, L.; Yang, M. Adv. Synth. Catal. 2015, 357, 1333– 1350. (b) Chen, Y. Chem. Eur. J. 2018, 24, 1–36.

4 (a) Shang, R.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2015, 137, 7660–7663. (b) Shang, R.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2016, 138, 10132–10135.

5 Cahiez, G.; Duplais, C.; Buendia, J. Chem. Rev. 2009, 109, 1434–1476.

6 (a) Morris, R. J.; Girolami, G. S. J. Am. Chem. Soc. 1988, 110, 6245–6246. (b) Morris, R. J.; Girolami, G. S. Organometallics 1991, 10, 792–799.

7 An initial experiment was performed by Takumi Yoshida.

8 For Mn-catalyzed homocoupling reaction using dihalogenated alkane as an oxidant, see: Zhou, Z.; Xue, W. J. Organomet. Chem. 2009, 694, 599–603.

9 For radical reaction using organomanganese via single electron transfer, see: (a) Nakao, J.; Inoue, R.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1997, 62, 1910–1911. (b) Inoue, R.; Nakao, J.; Shinokubo, H.; Oshima, K. Bull. Chem. Soc. Jpn. 1997, 7, 2039–2049.

10 Tamura, M.; Kochi, J. K. J. Organomet. Chem. 1971, 29, 111−129.

11 Cahiez, G.; Moyeux, A.; Buendia, J.; Duplais, C. J. Am. Chem. Soc. 2007, 129, 13788−13789.

12 For Rh-catalyzed sequential arylation of benzonitrile, see: Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2005, 7, 2229–2231.

13 Nobushige, K.; Hirano, K.; Satoh, T.; Miura, M. Tetrahedron 2015, 71, 6506–6512.

14 The reaction was performed by Hamad H. Al Mamari.

15 Forniés, J.; Martín, A.; Martín, L. F.; Menjón, B.; Zhen, H.; Bell, A.; Rhodes, L. F. Organometallics 2005, 24, 3266–3271.

16 Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923–2925.

17 Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen R. K.; Timmers F. J. Organometallics 1996, 15, 1518–1520.

18 Quinio, P.; Benischke, A. D.; Moyeux, A.; Cahiez, G.; Knochel, P. Synlett 2015, 26, 514–518.

19 Ackermann, L.; Lygin, A. V.; Hofmann, N. Angew. Chem. Int. Ed. 2011, 50, 6379– 6382.

20 Miyamura, S.; Araki, M.; Ota, Y.; Itoh, Y.; Yasuda, S.; Masuda, M.; Tniguchi, T.; Sowa, Y.; Sakai, T.; Suzuki, T.; Itami, K.; Yamaguchi, J. Org. Biomol. Chem. 2016, 14, 8576–8585.

21 Hyster, T. K.; Rovis, T. J. Am. Chem. Soc. 2010, 132, 10565–10569.

22 Shang, R.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2015, 137, 7660–7663.

23 Ackermann, L.; Lygin, A. V.; Hofmann, N. Org. Lett. 2011, 13, 3278–3281.

24 Miura, T.; Takahashi, Y.; Murakami, M. Chem. Commun. 2007, 3577–3579.

25 Lehmann, F.; Currier, E. A.; Olsson, R.; Hacksell, U.; Luthman, K. Bioorg. Med. Chem. 2005, 13, 3057–3068.

26 Lehmann, F.; Currier, E. A.; Olsson, R.; Ma, J.-N,; Burstein,E. S. Hacksell, U.; Luthman, K. Bioorg. Med. Chem. 2010, 18, 4844–4854.

27 Chen, X.; Li, J.-J.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 78–79.

28 Boissarie, P. J.; Hamilton, Z. E.; Lang, S.; Murphy, J. A.; Suckling, C. J. Org. Lett. 2011, 13, 6256–6259.

29 Asaumi, T.; Matsuo, T.; Fukuyama, T.; Ie, Y.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 4433–4440.

30 Nobuta, T.; Hirashima, S.; Tada, N.; Miura, T.; Itoh, A. Org. Lett. 2011, 13, 2576– 2579.

31 Baskin, J. M.; Wang, Z. Org. Lett. 2002, 4, 4423–4425.

32 Sheldrick, G. M. Acta Crystallogr A Found Adv 2015, 71, 3–8.

33 C. Kabuto, S. Akine, T. Nemoto, and E. Kwon, J. Cryst. Soc. Jpn., 2009, 51,218-224.