Notes and references

13 1 _{Martin, R. B. J. Chem. Educ. 1999, 76, 133.}

2 _{Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, John Wiley &} Sons: Hoboken, NJ, 2009.

3_{Metal-Catalyzed Cross-Coupling Reactions and More; de Meijere, A., Bräse, S., Oestreich,}

M., Eds.; Wiley-VCH: Weinheim, Germany, 2014.

4 _{For representative accounts and reviews, see (a) Beletskaya, I. P.; Cheprakov, A. V. Chem.}

Rev. 2000, 100, 3009–3066. (b) Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722–6737. (c) Negishi, E. Angew. Chem., Int. Ed. 2011, 50, 6738–6764.

5 _{For recent overviews, see (a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev.} 2013, 113, 5322–5363. (b) Schultz, D. M.; Yoon, T. P. Science2014, 343, 1239176. (c) Twilton, J.; Le, C.; Zhang, P.; Shaw, M. H.; Evans, R. W.; MacMillan, D. W. C. Nat. Rev.

Chem. 2017, 1, 0052. (d) Paria, S.; Reiser, O. ChemCatChem. 2014, 6, 2477–2483. 6 _{Klan, P.; Wirz, J. Photochemistry of organic compounds: From concepts to practice;}

Wiley: Chichester, U.K., 2009.

7 _{Fu, G. C. ACSCent. Sci. 2017, 3, 692–700.}

8 _{Creutz, S. E.; Lotito, K. J.; Fu, G. C.; Peters, J. C. Science2012, 338, 647–651.}

9 _{(a) Harkins, S. B.; Peters, J. C. J. Am. Chem. Soc. 2005, 127, 2030–2031. (b) Mankad, N.} P.; Rivard, E.; Harkins, S. B.; Peters, J. C. J. Am. Chem. Soc. 2005, 127, 16032–16033. (c) Miller, A. J. M.; Dempsey, J. L.; Peters, J. C. Inorg. Chem. 2007, 46, 7244–7246. (d) Harkins, S. B.; Mankad, N. P.; Miller, A. J. M.; Szilagyi, R. K.; Peters, J. C. J. Am. Chem.

Soc. 2008, 130, 3478–3485. (e) Mankad, N. P.; Harkins, S. B.; Antholine, W. E.; Peters, J.

C. Inorg. Chem. 2009, 48, 7026–7032. (f) Lotito, K. J.; Peters, J. C. Chem. Comm. 2010,

46, 3690–3692. (g) Deaton, J.; Switalski, S.; Kondakov, D.; Young, R.; Pawlik, T.; Giesen, D.; Harkins, S.; Miller, A.; Mickenberg, S.; Peters, J. C. J. Am. Chem. Soc. 2010, 132, 9499–9508.

10 _{Jones, G. O.; Liu, P.; Houk, K. N.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 6205–} 6213.

11 _{(a) Tye, J. W.; Weng, Z.; Johns, A. M.; Incarvito, C. D.; Hartwig, J. F. J.Am. Chem. Soc.} 2008, 130, 9971–9983. (b) Giri, R.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 15860– 15863.

12 _{For an independent study using a related approach, see Sagadevan, A.; Hwang, K. C. Adv.}

Synth. Catal. 2012, 354, 3421–3427.

13 _{(a) Bissember, A. C.; Lundgren, R. J.; Creutz, S. E.; Peters, J. C.; Fu, G. C. Angew. Chem.,}

14

Soc.2013, 135, 9548–9552. (c) Ziegler, D. T.; Choi, J.; Muñoz-Molina, J. M.; Bissember, A. C.; Peters, J. C.; Fu, G. C. J. Am. Chem. Soc.2013, 135, 13107–13112. (d) Do, H.-Q.; Bachman, S.; Bissember, A. C.; Peters, J. C.; Fu, G. C. J. Am. Chem. Soc.2014, 136, 2162– 2167. (e) Tan, Y.; Muñoz-Molina, J. M.; Fu, G. C.; Peters, J. C. Chem. Sci.2014, 5, 2831– 2835. (f) Ratani, T. S.; Bachman, S.; Fu, G. C.; Peters, J. C. J. Am. Chem. Soc.2015, 137, 13902–13907.

14 _{Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257–10274.} 15 _{Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451–3479.}

16 _{(a) Brown, D. G.; Boström, J. J. Med. Chem. 2016, 59, 4443–4458. (b) Schneider, N.;} Lowe, D. M.; Sayle, R. A.; Tarselli, M. A.; Landrum, G. A. J. Med. Chem. 2016, 54, 4385– 4402.

17 _{Kainz, Q. M.; Matier, C. M.; Bartoszewicz, A.; Zultanski, S. L.; Peters, J. C.; Fu, G. C.}

Science2016, 351, 681−684.

18 _{Carbazole is a suspected carcinogen according to the following study: Talhout, R.; Schulz,} T.; Florek, E.; Benthem, J. V.; Wester, P.; Opperhuizen, A. Int. J. Environ. Res. Publ.

Health. 2011, 8, 613–628.

19 _{(a) Patel, O. P. S.; Mishra, A.; Maurya, R.; Saini, D.; Pandey, J.; Taneja, I.; Raju, K. S. R.;} Kanojiya, S.; Shukla, S. K.; Srivastava, M. N.; Wahajuddin, M.; Tamrakar, A. K.; Srivastava, A, K.; Yadav, P. P. J. Nat. Prod. 2016, 79, 1276–1284. (b) Knölker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303–4427. (c) Schmidt, A. W.; Reddy, K. R. Knölker, H.-J. Chem. Rev. 2012, 112, 3193–3328.

20 _{Tsutsumi, L. S.; Gundisch, D.; Sun, D. Curr. Top. Med. Chem. 2016, 16, 1290–1313.} 21 _{(a) Morin, J.-F.; Leclerc, M.; Adès, D.; Slove, A. Macromol. RapidCommun. 2007, 28,}

1761–1775. (b) Wang, H.; Sheikh, A. D.; Feng, Q.; Li, F.; Chen, Y.; Yu, W.; Alarousu, E.; Ma, C.; Haque, M.; Shi, D.; Wang, Z.-S.; Mohammed, O. F.; Bakr, O. M.; Wu, T. ACS

Photonics, 2015, 2, 849–855.

22 _{Grazulevicius, J. V.; Strohriegl, P.; Pielichowski, J.; Pielichowski, K. Prog. Polym. Sci.} 2003, 28, 1297–1353.

23 _{Graebe, C.; Glaser, C. Ber. Dtsch. Chem. Ges. 1872, 5, 12.}

24 _{Murphy, J. J.; Bastida, D.; Paria, S.; Fagnoni, M.; Melchiorre, P. Nature2016, 532, 218–} 222.

25 _{For select examples, refer to (a) Plundrich, G. T.; Wadepohl, H. Gade, L. H. Inorg. Chem.} 2016, 55, 353–365. (b) Plundrich, G. T.; Wadepohl, H.; Clot, E.; Gade, L. H. Chem. –Eur.

15 26 _{For representative examples, see (a) Bezuidenhout, D. I.; Kleinhans, G.; Guisado-Barrios,} G.; Liles, D. C.; Ung, G.; Bertrand, G. Chem. Commun. 2014, 50, 2431–2433. (b) Gee, H.- C.; Lee, C.-H.; Jeong, Y.-H.; Jang, W.-D. Chem. Commun. 2011, 47, 11963–11965. (c) Grüger, N.; Rodriguez, L.-I.; Wadepohl, H.; Gade, L. H. Inorg. Chem. 2013, 52, 2050– 2059.

27 _{Higuchi, J.; Kuriyama, S.; Eizawa, A.; Arashiba, K.; Nakajima, K.; Nishibayashi, Y.}

DaltonTrans. 2018, 47, 1117–1121.

28 _{Bézier, D.; Guan, C.; Krogh-Jespersen, K.; Goldman, A. S.; Brookhart, M. Chem. Sci.} 2016, 7, 2579–2586.

29 _{Niwa, T.; Nakada, M. J. Am. Chem. Soc. 2012, 134, 13538–13541.}

30 _{Several transformations have relied on tridentate, carbazole-based chiral ligands for the} asymmetric three-component coupling reactions of organohalides in the presence of transition metal catalysts. For representative examples, see (a) Chen, W.; Yang, Q.; Zhou, T.; Tian, Q.; Zhang, G. OrgLett. 2015, 17, 5236–5239. (b) Xiong, Y.; Zhang, G. J. Am.

Chem. Soc. 2018, 140, 2735–2738. (c) Inoue, M.; Suzuki, T.; Nakada, M. J. Am. Chem.

Soc. 2003, 125, 1140–1141.

31 _{For other reports by the Fu and Peters groups on photoinduced copper catalysis, see (a)} Zhao, W.; Wurz, R. P.; Peters, J. C.; Fu, G. C. J. Am. Chem. Soc. 2017, 139, 12153–12156. (b) Matier, C. D.; Schwaben, J.; Peters, J. C.; Fu, G. C. J. Am. Chem. Soc. 2017, 139, 17707–17710.

16

Chapter 2. Mechanistic insights on copper-catalyzed alkylations of amines: