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Organic & Biomolecular Chemistry
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DOI: 10.1039/C7OB02579C
Journal Name
ARTICLE
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For selected reviews, see: (a) T. J. Snape, Chem. Soc. Rev.
2008, 37, 2452; (b) A. R.P. Henderson, J. R. Kosowan, and T.
E. Wood, Can. J. Chem., 2017, 95, 483.
For a recent review, see: L. El Kaïm and L. Grimaud, Eur. J.
Org. Chem., 2014, 7749.
photosensitizer. S.-F. Wang, X.-P. Cao and Y. Li, Angew.
Chem. Int. Ed. 2017, 56, 13089.
20 The emission spectrum of the compact fluorescence lamp
shows some irradiation at 487 nm (Figure S8 in ESI), but
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9
[Mes-Acr+] does not absorb light at
λ > 475 nm. A much
J. J. Koehler and W. N. Speckamp, Tetrahedron Lett., 1977,
18, 631.
better match is observed for the emission of the blue LED
lamp (around 456 nm) and the absorption of the
photocatalyst (Figures S7 and S9 in ESI).
10 For a recent review, see: I. Allart-Simon, S. Gérard and J.
Sapi, Molecules, 2016, 21, 878.
11 N.-C. C. Yang, P. Kumler and S. S. Yang, J. Org. Chem., 1972,
37, 4022.
12 H. Shinzawa, Y. Matsumoto, S. Tsuzuki, Y. Shimoi and H.
Suda, Vibrational Spectroscopy, 2015, 81, 131.
13 A. Hossian and R. Jana, Org. Biomol. Chem. 2016, 14, 9768.
21 For selected examples, see: (a) T. M. Nguyen, N. Manohar
and D. A. Nicewicz, Angew. Chem. Int. Ed., 2014, 53, 6198;
(b) M. A. Zeller, M. Riener and D. A. Nicewicz, Org. Lett.,
2014, 16, 4810; (c) N. A. Romero and D. A. Nicewicz, J. Am.
Chem. Soc., 2014, 136, 17024; (d) C. Cassani, G. Bergonzini
and C. –J. Wallentin, Org. Lett., 2014, 16, 4228.
14 For recent reviews, see: (a) J. Xuan, Z.-G. Zhang and W.-J. 22 For selected reviews, see: (a) Z. J. Garlets, J. D. Nguyen, C. R.
Xiao, Angew. Chem., Int. Ed., 2015, 54, 15632; (b) H. Fu and
Y. Jin, Asian J. Org. Chem., 2017, , 368.
15 For a recent comprehensive review, see: N. A. Romero and
D. A. Nicewicz, Chem. Rev., 2016, 116, 10075.
16 For recent examples of visible light-mediated radical Smiles
J. Stephenson, Isr. J. Chem., 2014, 54, 351; (b) D. Cambie, C.
Bottecchia, N. J. W. Straathof, V. Hessel, T. Noël, Chem. Rev.,
2016, 116, 10276.
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23 N. A. Romero and D. A. Nicewicz, J. Am. Chem. Soc., 2014,
136, 17024.
rearrangements, see: (a) J. J. Douglas, H. Albright, M. J. 24 J. Chateauneuf, J. Lusztyk and K. U. Ingold, J. Am. Chem. Soc.,
Sevrin, K. P. Cole and C. R. J. Stephenson, Angew. Chem. Int. 1988, 110, 2886.
Ed., 2015, 54, 14898; (b) J. J. Douglas, M. J. Sevrin, K. P. Cole 25 A similar mechanism for this transformation is proposed by
and C. R. J. Stephenson, Org. Process Res. Dev., 2016, 20
1148; (c) E. Brachet, L. Marzo, M. Selkti, B. König, P. Belmont,
Chem. Sci., 2016, , 5002.
,
Li and coworkers in reference 19, but the recycling of the
photocatalyst (PDI or Mes-Acr+) it is deduced without
experimental evidences.
7
17 For reviews, see: (a) S. Fukuzui, K. Ohkubo and T. Suenobu, 26 (a) For a comprehensive assay of the Marcus theory in
Acc. Chem. Res., 2014, 47, 1455; (b) S. Fukuzui and K.
Ohkubo, Org. Biomol. Chem., 2014, 12, 6059; (c) D. A.
Nicewicz and D. S. Hamilton, Synlett, 2014, 25, 1191. For the
seminal work, see: (d) S. Fukuzumi, H. Kotani, K. Ohkubo, S.
electron-transfer reactions, see: R. A. Marcus, Angew. Chem.
Int. Ed., 1993, 32, 1111. (b) For a more recent and closely
related example, see: K. Ohkubo, T. Kobayashi and S.
Fukuzumi, Angew. Chem. Int. Ed., 2011, 50, 8652.
Ogo, N. V. Tkachenko and H. Lemmetyinen, J. Am. Chem. Soc. 27 Given that for most of the substrates this BET is highly
2004, 126, 1600.
exergonic (e.g.: for 1a, ꢀGBET = -2.32 eV ), should be located
18 For previous work of our group in this context, see: (a) N. P.
Ramirez, I. Bosque and J. C. Gonzalez-Gomez, Org. Lett.,
2015, 17, 4550; (b) N. P. Ramirez and J. C. Gonzalez-Gomez,
Eur. J. Org. Chem. (special issue), 2017, 2154.
in the Marcus-inverted region, being thereby very slow. On
the contrary, for methoxylated substrates this BET is less
exergonic (e. g. : for 1e, , ꢀGBET = -1.62 eV), and likely to be
fast because should lie in the Marcus-normal region.
19 During the preparation of this manuscript it was reported a
similar radical Smiles rearrangement using PDI as
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