10.1002/cssc.201901725
ChemSusChem
FULL PAPER
Chem. Rev. 2016, 116, 9683-9747; f) D. Ravelli, S. Protti, M.
Maruoka, K. Morokuma, J. Org. Chem. 2015, 80, 9264-9271; c) S.
Selvakumar, R. Sakamoto, K. Maruoka, Chem. Eur. J. 2016, 22,
6552-6555.
Fagnoni, Chem. Rev. 2016, 116, 9850-9913; g) D. M. Schultz, T. P.
Yoon, Science 2014, 343, 985-993; h) Y.-M. Xi, H. Yi, A. Lei, Org.
Biomol. Chem. 2013, 11, 2387-2403; i) H. Yi, G. Zhang, H. Wang, Z.
Huang, J. Wang, A. K. Singh, A. Lei, Chem. Rev. 2017, 117, 9016-
9085.
[11] For extensive optimization and mechanistic experiments, see
Supporting Information.
[12] R. S. Mulliken, J. Phys. Chem. 1952, 56, 801-822.
[13] a) S. Farid, J. P. Dinnocenzo, P. B. Merkel, R. H. Young, D. Shukla, J.
Am. Chem. Soc. 2011, 133, 4791-4801; b) S. Farid, J. P. Dinnocenzo,
P. B. Merkel, R. H. Young, D. Shukla, G. Guirado, J. Am. Chem. Soc.
2011, 133, 11580-11587; c) M. Koch, G. Licari, E. Vauthey, J. Phys.
Chem. B 2015, 119, 11846-11857.
[2]
For selected reviews, see: a) M. Fagnoni, D. Dondi, D. Ravelli, A.
Albini, Chem. Rev. 2007, 107, 2725-2756; b) N. A. Romero, D. A.
Nicewicz, Chem. Rev. 2016, 116, 10075-10166; c) I. K. Sideri, E.
Voutyritsa, C. G. Kokotos, Org. Biomol. Chem. 2018, 16, 4596-4614;
For a selection of recent contributions, see: d) R. Brimioulle, T. Bach,
Science 2013, 342, 840-843; e) N. A. Romero, K. A. Margrey, N. E.
Tay, D. A. Nicewicz, Science 2015, 349, 1326-1330; f) I. Ghosh, T.
Ghosh, J. I. Bardagi, B. König, Science 2014, 346, 725-728; g) E.
Speckmeier, T. Fische, K. Zeitler, J. Am. Chem. Soc. 2018, 140,
15353-15365.
[14] a) E. Arceo, I. D. Jurberg, A. Alvarez-Fernandez, P. Melchiorre,
Nature Chem. 2013, 5, 750-756; b) L. Wozniak, J. J. Murphy, P.
Melchiorre, J. Am. Chem. Soc. 2015, 137, 5678-5681; c) M. Silvi, E.
Arceo, I. D. Jurberg, C. Cassani, P. Melchiorre, J. Am. Chem. Soc.
2015, 137, 6120-6123; d) J. J. Murphy, D. Bastida, S. Paria, M.
Fagnoni, P. Melchiorre, Nature 2016, 532, 218-222; e) A.
Bahamonde, P. Melchiorre, J. Am. Chem. Soc. 2016, 138, 8019-
8030.
[3]
(a) G. N. Papadopoulos, D. Limnios, C. G. Kokotos, Chem. Eur. J.,
2014, 20, 13811-13814; b) G. N. Papadopoulos, C. G. Kokotos,
Chem. Eur. J. 2016, 22, 6964-6967; c) G. N. Papadopoulos, C. G.
Kokotos, J. Org. Chem. 2016, 81, 7023-7028; d) D. Limnios, C. G.
Kokotos, Adv. Synth. Catal. 2017, 359, 323-328; e) N. Kaplaneris, A.
Bisticha, G. N. Papadopoulos, D. Limnios, C. G. Kokotos, Green
Chem. 2017, 19, 4451-4456.
[15] M. L. Spell, K. Deveneaux, C. G. Bresnahan, B. L. Bernard, W.
Sheffield, R. Kumar, J. R. Ragains, Angew. Chem. Int. Ed. 2016, 55,
6515-6519; Angew. Chem. 2016, 128, 6625-6629.
[16]
E. Arceo, E. Montroni, P. Melchiorre, Angew. Chem. Int. Ed. 2014,
53, 12064-12068; Angew. Chem. 2014, 126, 12260-12264.
F. Strieth-Kalthoff, M. J. James, M. Teders, L. Pitzera, F. Glorius,
Chem. Soc. Rev. 2018, 47, 7190-7202.
[4]
G. N. Papadopoulos, E. Voutyritsa, N. Kaplaneris, C. G. Kokotos,
Chem. Eur. J. 2018, 24, 1726-1731.
[17]
[5] For reviews, see: a) M. C. Willis, Chem. Rev. 2010, 110, 725-748; b) J.
C. Leung, M. J. Krische, Chem. Sci. 2012, 3, 2202-2209; For
selected examples, see: c) X. Yue, X. Qi, R. Bai, A. Lei, Y. Lan,
Chem. Eur. J. 2017, 23, 6419-6425; d) S. Tang, L. Zeng, Y. Liu, A.
Lei, Angew. Chem. 2015, 127, 16076-16079; Angew. Chem. Int. Ed.
2015, 54, 15850-15853.
[18] M. A. Cismesia, T. P. Yoon, Chem. Sci. 2015, 6, 5426-5434.
[19] N. F. Nikitas, I. Triandafillidi, C. G. Kokotos, Green Chem. 2019, 21,
669-674.
[20] W. Huang, B. C. Ma, H. Lu, R. Li, L. Wang, K. Landfester, K. A. I.
Zhang, ACS Catal. 2017, 7, 5438-5442.
[6]
For a review, see: A. T. Biju, N. Kuhl, F. Glorius, Acc. Chem. Res.
2011, 44, 1182-1195.
[21] N. J. Turro, Molecular Photochemistry, Benjamin, New York, 1965, p.
86.
[7]
a) M. S. Kharasch, W. H. Urry, B. M. Kuderna, J. Org. Chem. 1949,
14, 248-253; b) B. Fraser-Reid, R. C. Anderson, D. R. Hicks, D. L.
Walker, Can. J. Chem. 1977, 55, 3986-3995; c) D. Belotti, J. Cossy,
J. P. Pete, C. Portella, Tetrahedron Lett. 1985, 26, 4591-4594; d) K.
Kobayashi, M. Suzuki, H. Takeuchi, A. Konishi, H. Sakurai, H.
Suginome, J. Chem. Soc. Perkin Trans. 1 1994, 1099-1104; e) K.
Ogura, T. Arai, A. Kayano, M. Akazome, Tetrahedron Lett. 1999, 40,
2537-2540; f) J. Cossy, D. Belotti, Tetrahedron 2006, 62, 6459-
6594; g) M. Okada, K. Yamada, T. Fukuyama, D. Ravelli, M. Fagnoni,
I. Ryu, J. Org. Chem. 2015, 80, 9365-9369; h) G. Bergonzini, C.
Cassani, C.-J. Wallentin, Angew. Chem. 2015, 127, 14272-14275.
Angew. Chem. Int. Ed. 2015, 54, 14066-14069; i) G.-Z.Wang, R.
Shang, W.-M. Cheng, Y. Fu, Org. Lett. 2015, 17, 4830-4833.
a) S. Esposti, D. Dondi, M. Fagnoni, A. Albini, Angew. Chem. 2007,
119, 2583-2586; Angew. Chem. Int. Ed. 2007, 46, 2531-2534; b) S.
Protti, D. Ravelli, M. Fagnoni, A. Albini, Chem. Commun. 2009, 0,
7351-7353; c) D. Ravelli, M. Zema, M. Mella, M. Fagnoni, A. Albini,
Org. Biomol. Chem. 2010, 8, 4158-4164; d) L. Capaldo, R. Riccardi,
D. Ravelli, M. Fagnoni, ACS Catal. 2018, 8, 304-309. e) J.-J. Zhao,
H.-H. Zhang, X. Shen, S. Yu, Org. Lett. 2019, 21, 913-916.
[22] Z.-P. Lin, W.A. Aue, Spectrochimica Acta Part A 2000, 56, 111-117.
[23] M. Cocivera, A. M. Trozzolo, J. Am. Chem. Soc. 1970, 6, 1772-1774.
[24] G. L. Closs, D. R. Paulson, J. Am. Chem. Soc. 1970, 24, 7229-7231.
[25]
R. S. Davidson, J. Edwards, S. K. Warburton, J. Chem. Soc. Perkin
Trans. 1 1976, 1511-1514.
[26] Y. Zhang, K. B. Teuscher, H. Ji, Chem. Sci. 2016, 7, 2111-2118.
[8]
[9]
a) R. J. Fitzmaurice, J. M. Ahern, S. Caddick, Org. Biomol. Chem.
2009, 7, 235-237; b) V. Chudasama, R. J. Fitzmaurice, J. M. Ahern,
S. Caddick, Chem. Commun. 2010, 46, 133-135; c) V. Chudasama,
R. J. Fitzmaurice, S. Caddick, Nature Chem. 2010, 2, 592-596; d) X.-
Z. Fan, J.-W. Rong, H.-L. Wu, Q. Zhou, H.-P. Deng, J. Da, T. C. W.
Xue, L.-Z. Wu, H.-R. Tao, J. Wu, Angew. Chem. 2018, 130, 8650-
8654; Angew. Chem. Int. Ed. 2018, 57, 8514-8518; e) L. Zhang, G.
Zhang, Y. Li, S. Wang, A. Lei, Chem. Commun. 2018, 54, 5744-
5747.
[10]
a) S. A. Moteki, A. Usui, S. Selvakumar, T. Zhang, K. Maruoka,
Angew. Chem. 2014, 126, 11240-1124; Angew. Chem. Int. Ed. 2014,
53, 11060-11064; b) J. Jiang, R. Ramozzi, S. Moteki, A. Usui, K.
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