Please do not adjust margins
ChemComm
Page 4 of 5
COMMUNICATION
Journal Name
P. Yoon, Science, 2014, 343, 985-993. (d) L. Marzo, S. K. 15. For related reviews, see: (a) M. D. Levin, S. KVimiew, Aarnticdle OF.nliDne.
Pagire, O. Reiser, and B. König, Angew. Chem., Int. Ed., 2018,
57, 10034-10072.
DOI: 10.1039/C9CC00987F
P. Zhang, M. H. Shaw, R. W. Evans and D. W. C. MacMillan,
Nat. Rev. Chem., 2017, 1, 0052. For two pioneering works
on dual photoredox/Ni catalysis, see: (c) J. C. Tellis, D. N.
Primer, and G. A. Molander, Science, 2014, 345, 433-436. (d)
Z. Zuo, D. T. Ahneman, J. Chu, J. A. Terrett, A. G. Doyle, and
D. W. C. MacMillan, Science, 2014, 345, 437-440.
2. For selected reviews on homogenous visible light
photocatalysis with transition metal complexes, see: (a) C. K.
Prier, D. A. Rankic, and D. W. C. MacMillan, Chem. Rev.,
2013, 113, 5322-5363. With organic dyes, see: (b) N. A.
Romero and D. A. Nicewicz, Chem. Rev., 2016, 116, 10075-
10166.
3. For selected reviews on heterogeneous visible light
photocatalysis with semiconductors, see: (a) M.
Cherevatskaya, and B. König. Russ. Chem. Rev., 2014, 83,
183-195. (b) X. Lang, X. Chen, and J. Zhao, Chem. Soc. Rev.,
2014, 43, 473-486. (c) J. Chen, J. Cen, X. Xu, and X. Li, Catal.
Sci. Technol., 2016, 6, 349-362.
4. (a) I. T. Horváth and M. M. Kirchhoff, Acc. Chem. Res. 2002,
35, 686-694. (b) I. T. Horváth and P. T. Anastas, Chem. Rev.
2007, 107, 2169-2173.
5. (a) X. Chen and S. S. Mao, Chem. Rev., 2007, 107, 2891-1959.
(b) R. M. Navarro Yerga, M. C. Álvarez-Galván, F. del Valle, J.
A. Villoria de La Mano, and J. L. G. Fierro, ChemSusChem.,
2009, 2, 471-485 (c) A. Kudo and Y. Miseki, Chem. Soc. Rev.,
2009, 38, 253-278.
6. M. Cherevatskaya, M. Neumann, S. Füldner, C. Harlander, S.
Kümmel, S. Dankesreiter, A. Pfitzner, K. Zeitler, and B. König,
Angew. Chem. Int. Ed., 2012, 51, 4062-4066.
7. J. A. Caputo, L. C. Frenette, N. Zhao, K. L. Sowers, T. D. Krauss,
and D. J. Weix, J. Am. Chem. Soc., 2017, 139, 4250-4253.
8. (a) M. N. Hopkinson, B. Sahoo, J.-L. Li, and F. Glorius, Chem.
Eur. J., 2014, 20, 3874-3886. (b) K. L. Skubi, T. R. Blum, and T.
P. Yoon, Chem. Rev., 2016, 116, 10035-10074.
16. (a) S. Z. Tasker, and T. F. Jamison, J. Am. Chem. Soc., 2015,
137, 9531-9534. (b) E. B. Corcoran, M. T. Pirnot, S. Lin, S. D.
Dreher, D. A. DiRocco, I. W. Davies, S. L. Buchwald, and D. W.
C. MacMillan, Science, 2016, 353, 279-283. (c) M. S.
Oderinde, N. H. Jones, A. Juneau, M. Frenette, B. Aquila, S.
Tentarelli, D. W. Robbins, and J. W. Johannes, Angew. Chem.
Int. Ed., 2016, 55, 13219-13223. (d) T. Kim, S. J. McCarver, C.
Lee, and D. W. C. MacMillan, Angew. Chem., Int. Ed., 2018,
57, 3488-3492. (e) Y. Du, R. M. Pearson, C. H. Lim, S. M.
Sartor, M. D. Ryan, H. S. Yang, N. H. Damrauer and G. M.
Miyake, Chem.–Eur.J., 2017, 23, 10962-10968. (f) Z. Huang,
K. Xie, G. Meng, J. Ma, D. Xue and J. Yang, CN108409618,
2018, A. For the nickel catalyzed C-N coupling with near UV
light, see: (g) C. H. Lim, M. Kudisch, B. Liu, and G. M. Miyake,
J. Am. Chem. Soc., 2018, 140, 7667-7673. For the C-N
coupling with dual nickel/electrochemical catalysis, see: (h)
C. Li, Y. Kawamata, H. Nakamura, J. C. Vantourout, Z. Liu, Q.
Hou, D. Bao, J. T. Starr, J. Chen, M. Yan and P. S. Baran,
Angew. Chem., Int. Ed., 2017, 56, 13088-13093.
17. (a) J. A. Terrett, J. D. Cuthbertson, V. W. Shurtleff, and D. W.
C. MacMillan, Nature, 2015, 524, 330-334. (b) E. R. Welin, C.
Le, D. M. Arias-Rotondo, J. K. McCusker, and D. W. C.
MacMillan, Science, 2017, 355, 380-385.
9. (a) F. Parrino, A. Ramakrishnan, and H. Kisch, Angew. 18. Z. Chai, T.-T. Zeng, Q. Li, L.-Q. Lu, W.-J. Xiao, and D. Xu, J. Am.
Chem.Int. Ed., 2008, 47, 7107-7109. (b) X. Chen, J. Zhang, X. Chem. Soc., 2016, 138, 10128-10131.
Fu, M. Antonietti, and X. Wang, J. Am. Chem. Soc. 2009, 131, 19. (a) J.-R. Chen, X.-Q. Hu, L.-Q. Lu, and W.-J. Xiao, Acc. Chem.
11658-11659. (c) Y. Zhang, N. Zhang, Z.-R. Tang, and Y.-J. Xu,
Chem. Sci., 2012, 3, 2812-2822; (d) V. T. Bhat, P. A. Duspara,
S. Seo, N. S. B. A. Bakar, and M. F. Greaney, Chem. Commun.,
2015, 51, 4383-4385.
Res., 2016, 49, 1911−1923. (b) W. Ding, L.-Q. Lu, Q.-Q. Zhou,
Y. Wei, J.-R. Chen, and W.-J. Xiao, J. Am. Chem. Soc., 2017,
139, 63-66. (c) Y.-Y. Liu, X.-Y. Yu, J.-R. Chen, M.-M. Qiao, X.
Qi, D.-Q. Shi, and W.-J. Xiao, Angew. Chem. Int. Ed., 2017,
56, 9527-9531.
10. For selected examples on Quantum Dots catalyzed organic
reactions, see: (a) X.-B. Li, Z.-J. Li, Y.-J. Gao, Q.-Y. Meng, S. 20. (a) L.-Q. Lu, T.-R. Li, Q. Wang, and W.-J. Xiao, Chem. Soc. Rev.,
Yu, R.-G. Weiss, C.-H. Tung, and L.-Z. Wu, Angew. Chem. Int.
Ed., 2014, 53, 2085-2089. (b) L.-M. Zhao, Q.-Y. Meng, X.-B.
Fan, C. Ye, X.-B. Li, B. Chen, V. Ramamurthy, C.-H. Tung, and
2017, 46, 4135-4149. (b) M.-M. Li, Y. Wei, J. Liu, H.-W. Chen,
L.-Q. Lu, and W.-J. Xiao, J. Am. Chem. Soc., 2017, 139,
14707-14713.
L.-Z. Wu, Angew. Chem. Int. Ed., 2017, 56, 3020-3024. (c) Z. 21. (a) T. Mitkina, C. Stanglmair, W. Setzer, M. Gruber, H. Kisch,
Zhang, K. Edme, S. Lian, E. A. Weiss, J. Am. Chem. Soc. 2017,
139, 4246-4249.
and B. König, Org. Biomol. Chem., 2012, 10, 3556-3561. (b)
W. Zhao, C. Liu, L. Cao, X. Yin, H. Xu, B. Zhang, RSC Adv.,
2013, 3, 22944-22948.
11. (a) S. A. Lawrence, Amines: Synthesis Properties and
Applications (Cambridge Univ. Press, Cambridge, 2004); b) A. 22. N. Zhang, Y. Zhang, X. Pan, X. Fu, S. Liu, and Y.-J. Xu, J. Phys.
Ricci, Amino Group Chemistry: From Synthesis to the Life
Sciences (Wiley-VCH, Weinheim, 2008).
Chem. C, 2011, 115, 23501-23511.
23. G. Han, Y.-H. Jin, R. A. Burgess, N. E. Dickenson, X.-M. Cao,
and Y. Sun, J. Am. Chem. Soc., 2017, 139, 15584-15587.
12. (a) H. Fuwa, Total Synthesis of Marine Polycyclic Ether
Natural Products. In Toxins and Biologically Active 24. Price of NiCl2•6H2O vs NiCl2•glyme: 26.1 vs 473.8 CNY/g,
Compounds from Microalgae, Volume 1; CRC Press: Boca
Raton, FL, 2014, 348. (b) E. N. Pitsinos, V. P. Vidali, and E. A.
Price of CdS vs 5.1 vs 10,296 CNY/g. data from Sigma-
Aldrich.
Couladouros, Eur. J. Org. Chem., 2011, 1207-1222. (c) K. C. 25. Re-starting the C-N coupling reaction without addition of
Nicolaou, C. N. C. Boddy, S. Bräse, and N. Winssinger,
Angew. Chem. Int. Ed., 1999, 38, 2096-2152.
NiCl2•6H2O failed, indicating that the Ni catalyst is
homogeneous in solution.
13. (a) J. P. Wolfe, S. Wagaw, J. - F. Marcoux, and S. L. Buchwald, 26. Please see the details of condition optimizations for C-O
Acc. Chem. Res., 1998, 31, 805-818. (b) J. F. Hartwig, Acc.
coupling reactions in the Supporting Information.
Chem. Res., 1998, 31, 852-860. (c) P. Ruiz-Castillo, and S. L. 27. (a) B. Belleau, J. Burba, M. Pindell, and J. Reiffenstein,
Buchwald, Chem. Rev., 2016, 116, 12564-12649.
Science, 1961, 133, 102-104. (b) T. G. Gant, J. Med. Chem.,
2014, 57, 3595-3611. (c) A. Mullard, Nat. Rev. Drug Discov.,
2016, 15, 219-221.
14. (a) S. V. Ley, and A. W. Thomas, Angew. Chem. Int. Ed., 2003,
42, 5400-5449 (b) C. Sambiagio, S. P. Marsden, A. J. Blacker,
and P. C. McGowan, Chem. Soc. Rev., 2014, 43, 3525-3550.
28. L. Yang, Z. Huang, G. Li, W. Zhang, R. Cao, C. Wang, J. Xiao,
and D. Xue, Angew. Chem. Int. Ed., 2018, 57, 1968-1972.
4 | J. Name., 2015, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins