Organic Letters
Letter
6, 54−65. (d) Fountoulaki, S.; Daikopoulou, V.; Gkizis, P. L.;
Tamiolakis, I.; Armatas, G. S.; Lykakis, I. N. ACS Catal. 2014, 4,
3504−3511. (e) Gkizis, P. L.; Stratakis, M.; Lykakis, I. N. Catal.
Commun. 2013, 36, 48−51.
(10) (a) Kallitsakis, M.; Loukopoulos, E.; Abdul-Sada, A.; Tizzard,
G. J.; Coles, S. J.; Kostakis, G. E.; Lykakis, I. N. Adv. Synth. Catal.
2017, 359, 138−145. (b) Andreou, D.; Kallitsakis, M. G.;
Loukopoulos, E.; Gabriel, C.; Kostakis, G. E.; Lykakis, I. N. J. Org.
Chem. 2018, 83, 2104−2113.
(11) (a) Tzirakis, M. D.; Lykakis, I. N.; Orfanopoulos, M. Chem. Soc.
Rev. 2009, 38, 2609−2621. (b) Symeonidis, T. S.; Athanasoulis, A.;
Ishii, R.; Uozumi, Y.; Yamada, Y. M. A.; Lykakis, I. N.
ChemPhotoChem. 2017, 1, 479−484.
Foundation for Research and Innovation (HFRI) and the
General Secretariat for Research and Technology (GSRT)
under Grant Agreement No. [776] “PhotoDaLu” (KA97507).
We thank Prof. K. S. Triantafyllidis (Department of Chemistry,
AUTH) for performing the GC−TCD experiments. We thank
Dr. C. Gabriel (HERACLES Research Center, KEDEK,
Laboratory of Environmental Engineering (EnvE-Lab),
Department of Chemical Engineering, AUTH, Greece) for
performing and analyzing the HRMS experiments. I.N.L.
acknowledges the Empirikeion Foundation for financial
support of the photoapparatus.
(12) (a) Kaneko, C.; Yamada, S.; Yokoe, I.; Hata, N.; Ubukata, Y.
Tetrahedron Lett. 1966, 7, 4729−4733. (b) Hashimoto, S.; Sunamoto,
J.; Fujii, H.; Kano, K. Bull. Chem. Soc. Jpn. 1968, 41, 1249−1251.
(c) Hashimoto, S.; Kano, K. Tetrahedron Lett. 1970, 11, 3509−3512.
(d) Hashimoto, S.; Kano, K. Bull. Chem. Soc. Jpn. 1972, 45, 549−553.
(13) A further set of experiments with electron-withdrawing and
electron-donating substituted nitroarenes was performed in MeOH
(14) (a) Marin, M.; Miranda, M. A.; Marin, M. L. Catal. Sci. Technol.
2017, 7, 4852−4858. (b) Sakamoto, H.; Imai, J.; Shiraishi, Y.; Tanaka,
S.; Ichikawa, S.; Hirai, T. ACS Catal. 2017, 7, 5194−5201.
(15) (a) Kumar, P. Pharmacology and Therapeutics for Dentistry, 7th
ed.; Elsevier, 2017, 457−487. (b) Qu, Y.; Spain, J. C. Environ.
Microbiol. 2011, 13, 1010−1017. (c) Singh, R.; Manjunatha, U.;
Boshoff, H. I.; Ha, Y. H.; Niyomrattanakit, P.; Ledwidge, R.; Dowd,
C. S.; Lee, I. Y.; Kim, P.; Zhang, L.; Kang, S.; Keller, T. H.; Jiricek, J.;
Barry, C. E., 3rd Science 2008, 322, 1392−1395.
(16) (a) McClelland, R. A.; Panicucci, R.; Rauth, A. M. J. Am. Chem.
Soc. 1987, 109, 4308. (b) Corbett, M. D.; Chipko, B. R. Antimicrob.
Agents Chemother. 1978, 13, 193−198. (c) Lu, H.; Chanco, E.; Zhao,
H. Tetrahedron 2012, 68, 7651−7654. (d) Jakubec, P.; Urbanova, V.;
Medrikova, Z.; Zboril, R. Chem. - Eur. J. 2016, 22, 14279−14284.
(17) Selected reports on the photochemistry of nitroarenes:
(a) Wubbels, G. G.; Snyder, E. J.; Coughlin, E. B. J. Am. Chem. Soc.
REFERENCES
■
(1) The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids;
Rappoport, Z., Liebman, J. F.; John Wiley & Sons, Ltd., 2009.
(2) (a) Boymans, E. H.; Witte, P. T.; Vogt, D. Catal. Sci. Technol.
2015, 5, 176−183. (b) Rong, Z.; Du, W.; Wang, Y.; Lu, L. Chem.
Commun. 2010, 46, 1559−1561. (c) Takenaka, Y.; Kiyosu, T.; Choi,
J.-C.; Sakakura, T.; Yasuda, H. Green Chem. 2009, 11, 1385−1390.
(3) (a) Doherty, S.; Knight, J. G.; Backhouse, T.; Summers, R. J.;
Abood, E.; Simpson, W.; Paget, W.; Bourne, R. A.; Chamberlain, T.
W.; Stones, R.; Lovelock, K. R. J.; Seymour, J. M.; Isaacs, M. A.;
Hardacre, C.; Daly, Η.; Rees, N. H. ACS Catal. 2019, 9, 4777−4791.
(b) Prakash, P.; De Masi, D.; Geertsen, V.; Miserque, F.; Li, H.;
Namboothiri, I. N. N.; Gravel, E.; Doris, E. Chemistry Select 2017, 2,
5891−5894. (c) Jawale, D. V.; Gravel, E.; Boudet, C.; Shah, N.;
Geertsen, V.; Li, H.; Namboothiri, I. N. Ν.; Doris, E. Chem. Commun.
2015, 51, 1739−1742. (d) Hojczyk, K. N.; Feng, P.; Zhan, C.; Ngai,
M.-Y. Angew. Chem., Int. Ed. 2014, 53, 14559−14563. (e) Shil, A. K.;
Das, P. Green Chem. 2013, 15, 3421−3428.
(4) (a) Kou, J.; Lu, C.; Wang, J.; Chen, Y.; Xu, Z.; Varma, R. S.
Chem. Rev. 2017, 117, 1445−1514. (b) Capaldo, L.; Ravelli, D. Eur. J.
Org. Chem. 2017, 2017, 2056−2071. (c) Friedmann, D.; Hakki, A.;
Kim, H.; Choi, W.; Bahnemann, D. Green Chem. 2016, 18, 5391−
5411.
(5) (a) Nabid, M. R.; Nazaru, N.; Asadi, S.; Heravi, M. M.; Sedghi,
R. Curr. Org. Chem. 2016, 20, 696−734. (b) Kadam, H. K.; Tilve, S.
G. RSC Adv. 2015, 5, 83391−83407.
(6) Recent photocatalytic hydrogenation processes: (a) Hao, C.-H.;
Guo, X.-N.; Sankar, M.; Yang, H.; Ma, B.; Zhang, Y.; Tong, X.; Jin, G.;
Guo, X.-Y. ACS Appl. Mater. Interfaces 2018, 10, 23029−23036.
(b) Yu, Z.; Chen, Z.; Chen, Y.; Peng, Q.; Lin, R.; Wang, Y.; Shen, R.;
Cao, X.; Zhuang, Z.; Li, Y. Nano Res. 2018, 11, 3730−3738.
(7) Recent photocatalytic transfer hydrogenation processes:
(a) Amanchi, S. R.; Kumar, K. V. A.; Lakshminarayana, B.;
Satyanarayana, G.; Subrahmanyam, C. New J. Chem. 2019, 43,
748−754. (b) Todorov, A. R.; Aikonen, S.; Muuronen, M.; Helaja, J.
Org. Lett. 2019, 21, 3764−3768. (c) Piggott, E. K.; Hope, T. O.;
Crabbe, B. W.; Jalbert, P.-M.; Orlova, G.; Hallett-Tapley, G. L. Catal.
Sci. Technol. 2017, 7, 5758−5765. (d) Xiao, Q.; Sarina, S.; Waclawik,
E. R.; Jia, J.; Chang, J.; Riches, J. D.; Wu, H.; Zheng, Z.; Zhu, H. ACS
Catal. 2016, 6, 1744−1753. (e) Tsutsumi, K.; Uchikawa, F.; Sakai, K.;
Tabata, K. ACS Catal. 2016, 6, 4394−4398. (f) Yang, X.-Y.; Chen, B.;
Zheng, L.-Q.; Wu, L.-Z.; Tung, C.-H. Green Chem. 2014, 16, 1082−
1086.
̈
1988, 110, 2543−2548. (b) Dopp, D.; Topics, D. Top. Curr. Chem.
1975, 55, 49−85. (c) Frolov, A. N.; Kuznetsova, N. A.; Eltsov, A. V.
Russ. Chem. Rev. 1976, 45, 1024−1034. (d) Cu, A.; Testa, A. C. J. Am.
Chem. Soc. 1974, 96, 1963−1965. (e) Barltrop, J. A.; Bunce, N. J.;
Thomson, A. J. Chem. Soc. C 1968, 1467−1474. (f) Hurley, R.; Testa,
A. C. J. Am. Chem. Soc. 1966, 88, 4330−4332.
(18) (a) Steudel, E.; Posdorfer, J.; Schindler, R. N. Electrochim. Acta
1995, 40, 1587−1594. (b) Huang, Y.; Lessard, J. Electroanalysis 2016,
28, 2716−2727.
(19) Selected reports on the photochemical decomposition of
hydrazine: (a) Lambert, C. E.; Shank, R. C. Carcinogenesis 1988, 9,
65−70. (d) Hawkins, W. G.; Houston, P. L. J. Phys. Chem. 1982, 86,
704−709. (g) Arvis, M.; Devillers, C.; Gillois, M.; Curtat, M. J. Phys.
Chem. 1974, 78, 1356−1360. (h) Stief, L. J.; DeCarlo, V. J. J. Chem.
Phys. 1966, 44, 4638−4639.
(20) King, D. M.; Bard, A. J. J. Am. Chem. Soc. 1965, 87, 419−423.
(8) (a) Chen, G.-J.; Xin, W.-L.; Wang, J.-S.; Cheng, J.-Y.; Dong, Y.-
B. Chem. Commun. 2019, 55, 3586−3589. (b) Mondal, B.; Mukherjee,
P. S. J. Am. Chem. Soc. 2018, 140, 12592−12601. (c) Xu, Y.; Chen, Y.;
Fu, W.-F. ACS Omega 2018, 3, 1904−1911. (d) Chaiseeda, K.;
Nishimura, S.; Ebitani, K. ACS Omega 2017, 2, 7066−7070. (e) Guo,
X.; Hao, C.; Jin, G.; Zhu, H.-Y.; Guo, X.-Y. Angew. Chem., Int. Ed.
2014, 53, 1973−1977. (f) Zhu, H.; Ke, X.; Yang, X.; Sarina, S.; Liu, H.
Angew. Chem., Int. Ed. 2010, 49, 9657−9661.
(9) (a) Iordanidou, D.; Zarganes-Tzitzikas, T.; Neochoritis, C. G.;
̈
Domling, A.; Lykakis, I. N. ACS Omega 2018, 3, 16005−16013.
(b) Papadas, I. T.; Fountoulaki, S.; Lykakis, I. N.; Armatas, G. S.
Chem. - Eur. J. 2016, 22, 4600−4607. (c) Andreou, D.; Iordanidou,
D.; Tamiolakis, I.; Armatas, G. S.; Lykakis, I. N. Nanomaterials 2016,
E
Org. Lett. XXXX, XXX, XXX−XXX