Organic Letters
Letter
(11) Peralta-Hernandez, E.; Cortezano-Arellano, O.; Cordero-Vargas,
A. Tetrahedron Lett. 2011, 52, 6899.
(12) Cao, L.; Li, C. Tetrahedron Lett. 2008, 49, 7380.
(13) Metzger, J. O.; Mahler, R. Angew. Chem., Int. Ed. Engl. 1995, 34,
902.
(14) Yorimitsu, H.; Wakabayashi, K.; Shinokubo, H.; Oshima, K. Bull.
Chem. Soc. Jpn. 2001, 74, 1963.
(15) Zhang, M.; Li, W.; Duan, Y.; Xu, P.; Zhang, S.; Zhu, C. Org. Lett.
2016, 18, 3266.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We gratefully acknowledge financial support through the Latsis
Foundation programme “EPISTHMONIKES MELETES 2015”
(PhotoOrganocatalysis: Development of new environmentally
friendly methods for the synthesis of compounds for the
pharmaceutical and chemical industry). We also thank Prof. V.
Constantinou from the Agricultural University of Athens for
access to the fluorescence spectrometer. I.T. thanks the
Hellenic Foundation for Research and Innovation (ΕΛΙΔΕΚ),
and M.G.K. thanks the National Scholarship Foundation (IKY)
for financial support. COST Action C−H Activation in Organic
Synthesis (CHAOS) CA15106 is acknowledged for helpful
discussions.
(16) (a) Pertino, M. W.; Theoduloz, C.; Rodriguez, J. A.; Yanez, T.;
Lazo, V.; Schmeda-Hirschmann, G. J. Nat. Prod. 2010, 73, 639.
(b) Cooke, R. C.; Capone, D. L.; van Leeuwen, K. A.; Elsey, G. M.;
Sefton, M. A. J. Agric. Food Chem. 2009, 57, 348. (c) Jogi, A.; Paju, A.;
Pehk, T.; Kailas, T.; Muurisepp, A.-M.; Lopp, M. Tetrahedron 2009,
65, 2959.
(17) (a) Dohi, T.; Takenaga, N.; Goto, A.; Maruyama, A.; Kita, Y.
Org. Lett. 2007, 9, 3129. (b) Gooβen, L. J.; Ohlmann, D. M.; Dierker,
M. Green Chem. 2010, 12, 197. (c) Li, J.; Yang, S.; Jiang, H.; Wu, W.;
Zhao, J. J. Org. Chem. 2013, 78, 12477. (d) Triandafillidi, I.;
Raftopoulou, M.; Savvidou, A.; Kokotos, C. G. ChemCatChem 2017,
9, 4120.
(18) Shu, C.; Liu, M.-Q.; Sun, Y.-Z.; Ye, L.-W. Org. Lett. 2012, 14,
4958.
(19) (a) Xie, X.; Stahl, S. S. J. Am. Chem. Soc. 2015, 137, 3767.
(b) Kreimerman, S.; Ryu, I.; Minakata, S.; Komatsu, M. Org. Lett.
2000, 2, 389.
(20) (a) Papadopoulos, G. N.; Limnios, D.; Kokotos, C. G. Chem. -
Eur. J. 2014, 20, 13811. (b) Papadopoulos, G. N.; Kokotos, C. G. J.
Org. Chem. 2016, 81, 7023. (c) Papadopoulos, G. N.; Kokotos, C. G.
Chem. - Eur. J. 2016, 22, 6964. (d) Limnios, D.; Kokotos, C. G. Adv.
Synth. Catal. 2017, 359, 323. (e) Kaplaneris, N.; Bisticha, A.;
Papadopoulos, G.; Limnios, D.; Kokotos, C. G. Green Chem. 2017,
19, 4451.
REFERENCES
■
(1) (a) Kharasch, M. S.; Jensen, E. V.; Urry, W. H. Science 1945, 102,
128. (b) Kharasch, M. S.; Skell, P. S.; Fisher, P. J. Am. Chem. Soc. 1948,
70, 1055.
(2) (a) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org.
Chem. 1989, 54, 1826. (b) Curran, D. P.; Chang, C.-T. J. Org. Chem.
1989, 54, 3140. (c) Curran, D. P.; Chen, M.-H.; Spletzer, E.; Seong, C.
M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872. (d) Curran, D. P.;
Seong, C. M. J. Am. Chem. Soc. 1990, 112, 9401. (e) Curran, D. P.;
Tamine, J. J. Org. Chem. 1991, 56, 2746. (f) Curran, D. P.; Kim, D.
Tetrahedron 1991, 47, 6171. (g) Curran, D. P.; Kim, D.; Ziegler, C.
Tetrahedron 1991, 47, 6189.
(3) (a) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K. J.
Org. Chem. 1998, 63, 8604. (b) Yorimitsu, H.; Nakamura, T.;
Shinokubo, H.; Oshima, K.; Omoto, K.; Fujimoto, H. J. Am. Chem. Soc.
2000, 122, 11041. (c) Yorimitsu, H.; Shinokubo, H.; Matsubara, S.;
Oshima, K.; Omoto, K.; Fujimoto, H. J. Org. Chem. 2001, 66, 7776.
(4) (a) Renaud, P.; Ollivier, C.; Panchaud, P. Angew. Chem., Int. Ed.
2002, 41, 3460. (b) Panchaud, P.; Ollivier, C.; Renaud, P.; Zigmantas,
S. J. Org. Chem. 2004, 69, 2755. (c) Chabaud, L.; Landais, Y.; Renaud,
P. Org. Lett. 2005, 7, 2587. (d) Schar, P.; Renaud, P. Org. Lett. 2006, 8,
1569. (e) Weidner, K.; Giroult, A.; Panchaud, P.; Renaud, P. J. Am.
Chem. Soc. 2010, 132, 17511.
(21) For extensive optimization studies and mechanistic studies, see
(22) Cismesia, M. A.; Yoon, T. P. Chem. Sci. 2015, 6, 5426.
(23) For previous mechanistic studies of organic reactions with
HRMS from our group, see: (a) Kaplaneris, N.; Spyropoulos, C.;
Kokotou, M. G.; Kokotos, C. G. Org. Lett. 2016, 18, 5800.
(b) Voutyritsa, E.; Theodorou, A.; Kokotou, M. G.; Kokotos, C. G.
Green Chem. 2017, 19, 1291. (c) Koutoulogenis, G.; Kokotou, M. G.;
Voutyritsa, E.; Limnios, D.; Kokotos, C. G. Org. Lett. 2017, 19, 1760.
(24) For selective mechanistic studies of organic reactions with
HRMS from other groups, see: (a) Bachle, F.; Duschmale, J.; Ebner,
C.; Pfaltz, A.; Wennemers, H. Angew. Chem., Int. Ed. 2013, 52, 12619.
(b) Bachle, F.; Fleischer, I.; Pfaltz, A. Adv. Synth. Catal. 2015, 357,
2247. (c) Isenegger, P. G.; Bachle, F.; Pfaltz, A. Chem. - Eur. J. 2016,
22, 17595. (d) Cai, Y.; Wang, J.; Zhang, Y.; Li, Z.; Hu, D.; Zheng, N.;
Chen, H. J. Am. Chem. Soc. 2017, 139, 12259. For other methods to
study photocatalytic mechanisms, see: (e) Su, Y.; Kuijpers, K. P. L.;
Konig, N.; Shang, M.; Hessel, V.; Noel, T. Chem. - Eur. J. 2016, 22,
12295. (f) Majek, M.; Filace, F.; Jacobi von Wangelin, A. Beilstein J.
Org. Chem. 2014, 10, 981.
(5) For books and reviews, see: (a) Pintauer, T.; Matyjaszewski, K.
Encyclopedia of Radicals; Wiley: Hoboken, 2012; Vol. 4, pp 1851−
1894. (b) Curran, D. P. Synthesis 1988, 1988, 489. (c) Kamigaito, M.;
Ando, T.; Sawamoto, M. Chem. Rev. 2001, 101, 3689.
(6) For selected examples and reviews, see: (a) Nicewicz, D. A.;
MacMillan, D. W. C. Science 2008, 322, 77. (b) Yoon, T. P.; Ischay, M.
A.; Du, J. Nat. Chem. 2010, 2, 527. (c) Tucker, J. W.; Stephenson, C.
R. J. J. Org. Chem. 2012, 77, 1617. (d) Prier, C. K.; Rankic, D. A.;
MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. (e) Skubi, K. L.;
Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, 116, 10035. (f) Romero, N.
A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075. (g) Karkas, M. D.;
Porco, J. A., Jr; Stephenson, C. R. J. Chem. Rev. 2016, 116, 9683.
(h) Ravelli, D.; Protti, S.; Fagnoni, M. Chem. Rev. 2016, 116, 9850.
(i) Cambie, D.; Bottecchia, C.; Straathof, N. J. W.; Hessel, V.; Noel, T.
Chem. Rev. 2016, 116, 10276.
(25) Naumann, R.; Kerzig, C.; Goez, M. Chem. Sci. 2017, 8, 7510.
(7) (a) Nguyen, J. D.; Tucker, J. W.; Konieczynska, M. D.;
Stephenson, C. R. J. J. Am. Chem. Soc. 2011, 133, 4160. (b) Wallentin,
C.-J.; Nguyen, J. D.; Finkbeiner, P.; Stephenson, C. R. J. J. Am. Chem.
Soc. 2012, 134, 8875.
(8) Pirtsch, M.; Paria, S.; Matsuno, T.; Isobe, H.; Reiser, O. Chem. -
Eur. J. 2012, 18, 7336.
(9) (a) Arceo, E.; Montroni, E.; Melchiorre, P. Angew. Chem., Int. Ed.
2014, 53, 12064. (b) Magagnano, G.; Gualandi, A.; Marchini, M.;
Mengozzi, L.; Ceroni, P.; Cozzi, P. G. Chem. Commun. 2017, 53, 1591.
(10) (a) Kraus, A.; Landgrebe, K. Tetrahedron Lett. 1984, 25, 3939.
(b) Dange, N. S.; Robert, F.; Landais, Y. Org. Lett. 2016, 18, 6156.
(c) Wang, J.; Li, C. J. Org. Chem. 2002, 67, 1271.
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