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Chemical Science
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ARTICLE
Journal Name
9
Livingstone and G. Tennant, J. Chem.DSOoIc:.10C.1h0e3m9/.DC0SoCm0m21u3n4.B,
1973, 96–97; (b) I. W. Harvey, M. D. McFarlane, D. J. Moody
and D. M. Smith, J. Chem. Soc. Perkin. Trans. I, 1988, 1939–
1943; (c) J. M. Gardiner and J. Procter, Tetrahedron Lett., 2001
42, 5109–5111; (d) J. M. Gardiner, A. D. Goss, T. Majid, A.
D. Morley, R. G. Pritchard and J. E. Warren, Tetrahedron Lett.,
2002, 43, 7707–7710; (e) N. H. Ansari and B. C. G. Söderberg,
Tetrahedron Lett., 2017, 58, 4717–4720; (f) N. H. Ansari, A.
Notes and references
1
For selected reviews on metal-catalyzed C–H functionalization
reactions, see: (a) R. R. Karimov and J. F. Hartwig, Angew.
Chem., Int. Ed., 2018, 57, 4234–4241; (b) P. Gandeepan and L.
,
Ackermann, Chem, 2018,
Park and C.-H. Jun, Chem. Rev., 2017, 117, 8977–9015; (d) J.
Wencel-Delord and F. Glorius, Nat. Chem., 2013, , 369–375;
4, 199–222; (c) D.-S. Kim, W.-J.
5
(e) N. Kuhl, M. N. Hopkinson, J. Wencel-Delord and F.
Glorius, Angew. Chem., Int. Ed., 2012, 51, 10236–10254.
For selected reviews on photolytic C–H functionalization
reactions, see: (a) M. Uygur and O. García Mancheño, Org.
Biomol. Chem., 2019, 17, 5475–5489; (b) L. Revathi, L.
Ravindar, W.-Y. Fang, K. P. Rakesh and H.-L. Qin, Adv. Synth.
Catal., 2018, 360, 4652–4698; (c) C.-S. Wang, P. H. Dixneuf
and J.-F. Soulé, Chem. Rev., 2018, 118, 7532–7585; (d) L.
Capaldo and D. Ravelli, Eur. J. Org. Chem., 2017, 2056–2071;
(e) S. Protti, M. Fagnoni and D. Ravelli, ChemCatChem, 2015,
L. Jordan and B. C. G. Söderberg, Tetrahedron, 2017, 73
,
2
4811–4821.
10 For biological activities of N-hydroxybenzimidazoles, see: (a)
J. M. Gardiner, C. R. Loyns, A. Burke, A. Khan and N.
Mahmood, Bioorg. Med. Chem. Lett., 1995, 5, 1251–1254; (b)
T. E. Bowser, V. J. Bartlett, M. C. Grier, A. K. Verma, T.
Warchol, S. B. Levy and M. N. Alekshun, Bioorg. Med. Chem.
Lett., 2007, 17, 5652–5655; (c) O. K. Kim, L. K. Garrity-Ryan,
V. J. Bartlett, M. C. Grier, A. K. Verma, G. Medjanis, J. E.
Donatelli, A. B. Macone, S. Ken Tanaka, S. B. Levy and M. N.
Alekshun, J. Med. Chem., 2009, 52, 5626–5634; (d) M. C.
Grier, L. K. Garrity-Ryan, V. J. Bartlett, K. A. Klausner, P. J.
Donovan, C. Dudley, M. N. Alekshun, S. Ken Tanaka, M. P.
Draper, S. B. Levy and O. K. Kim, Bioorg. Med. Chem. Lett.,
2010, 20, 3380–3383; (e) W. Yue and H. Wang, Monatsh.
Chem., 2015, 146, 2079–2086; (f) A. E. Marsden, J. M. King,
M. A. Spies, O. K. Kim and T. L. Yahr, Antimicrob. Agents
Chemother., 2016, 60, 766–776.
7
, 1516–1523.
3
(a) V. Charushin and O. V. Chupakhin, Metal Free C–H
Functionalization of Aromatics. Nucleophilic Displacement of
Hydrogen, Springer International Publishing, Switzerland,
2014; (b) R. Narayan, K. Matcha and A. P. Antonchick, Chem.
Eur. J., 2015, 21, 14678–14693; (c) R. Narayan, S. Manna and
A. P. Antonchick, Synlett, 2015, 26, 1785–1803; (d) R.
Samanta, K. Matcha and A. P. Antonchick, Eur. J. Org. Chem.,
2013, 5769–5804.
4
5
J. C. K. Chu and T. Rovis, Angew. Chem., Int. Ed., 2018, 57
62–101.
For reviews of N-oxyl radicals as organoradical catalysts, see:
(a) K. Chen, P. Zhang, Y. Wang and H. Li, Green Chem., 2014,
16, 2344–2374; (b) S. Wertz, A and Studer, Green Chem.,
2013, 15, 3116–3134; (c) L. Melone and C. Punta, Beilstein J.
,
11 The use of N-hydroxybenzimidazole for amide condensation
reagents has been reported: (a) N. D. Kokare, R. R. Nagawade,
V. P. Rane and D. B. Shinde, Synthesis, 2007, 5, 766–772; (b)
N. D. Kokare, R. R. Nagawade, V. P. Rane and D. B. Shinde,
Tetrahedron Lett., 2007, 48, 4437–4440; (c) N. D. Kokare, D.
B. Shinde, J. Heterocyclic Chem., 2008, 45, 981–986.
Org. Chem., 2013, 9, 1296–1310; (d) F. Recupero and C. Punta,
Chem. Rev., 2007, 107, 3800–3842; (e) Y. Ishii and S.
Sakaguchi, Catal. Today, 2006, 117, 105–113; (f) R. A.
Sheldon, I and W. C. E. Arenas, Adv. Synth. Catal., 2004, 346
1051–1071; (g) Y. Ishii, S. Sakaguchi and T. Iwahama, Adv.
12 G. da Silva and J. W. Bozzelli, J. Phys. Chem. C, 2007, 111
,
5760–5765; (b) K. Chen, L. Jia, C. Wang, J. Yao, Z. Chen and
H. Li, ChemPhysChem, 2014, 15, 1673–1680; (c) K. Chen, J.
Yao, Z. Chen and H. Li, J. Catal., 2015, 331, 76–85.
13 For a review on acyl radical chemistry, see: C. Chatgilialoglu,
D. Crich, M. Komatsu and I. Ryu, Chem. Rev. 1999, 99, 1991–
2069.
14 (a) S. A. Moteki, A. Usui, S. Selvakumar, T. Zhang and K.
Maruoka, Angew. Chem., Int. Ed., 2014, 53, 11060–11064; (b)
S. Selvakumar, R. Sakamoto and K. Maruoka, Chem. Eur. J.,
2016, 22, 6552–6555; (c) S. Selvakumar, Q. K. Kang, N.
Arumugam, A. I. Almansour, R. S. Kumar and K. Maruoka,
Tetrahedron, 2017, 73, 5841–5846; (d) R. Sakamoto, N.
Hirama and K. Maruoka, Org. Biomol. Chem., 2018, 16, 5412–
5415.
,
Synth. Catal., 2001, 343, 393–427.
For selected examples of the use of NHPI and its derivatives
as organoradical catalysts, see: (a) S. Sakaguchi, Y. Nishiwaki,
6
T. Kitamura and Y. Ishii, Angew. Chem., Int. Ed., 2001, 40
222–224; (b) S. Tsujimoto, T. Iwahama, S. Sakaguchi and Y.
Ishii, Chem. Commun., 2001, 2352–2353; (c) T. Hirabayashi,
,
S. Sakaguchi and Y. Ishii, Angew. Chem., Int. Ed., 2004, 43
,
1120–1123; (d) Y. Amaoka, S. Kamijo, T. Hoshikawa and M.
Inoue, J. Org. Chem., 2012, 77, 9959–9969; (e) Y. Amaoka,
M. Nagatomo and M. Inoue, Org. Lett., 2013, 15, 2160–2163;
(f) K. Kiyokawa, K. Takemoto and S. Minakata, Chem.
Commun., 2016, 52, 13082–13085; (g) J. Liu, K.-F. Hu, J.-P.
Qu and Y.-B. Kang, Org. Lett., 2017, 19, 5593–5596; (h) S. H.
Combe, A. Hosseini, L. Song, H. Hausmann and P. R.
Schreiner, Org. Lett., 2017, 19, 6156–6159; (i) K. Kiyokawa,
R. Ito, K. Takemoto and S. Minakata, Chem. Commun., 2018,
54, 7609–7612; (j) M. Rafiee, F. Wang, D. P. Hruszkewycz, S.
S. Stahl, J. Am. Chem. Soc., 2018, 140, 22–25; (k) L. Ye, Y.
Tian, X. Meng, Q.-S. Gu, X.-Y. Liu, Angew. Chem., Int. Ed.
2020, 59, 1129–1133.
15 (a) Y. Ogiwara and N. Sakai, Angew. Chem., Int. Ed., 2020, 59
,
574–594; (b) N. Blanchard and V. Bizet, Angew. Chem., Int.
Ed., 2019, 58, 6814–6817; (c) G. Prabhu, N. Narendra,
Basavaprabhu, V. Panduranga and V. V. Sureshbabu, RSC Adv.
2015, , 48331–48362.
5
16 (a) N. Kielland, M. Vendrell, R. Lavilla and Y.-T. Chang,
Chem. Commun., 2012, 48, 7401–7403; (b) I. Dovgan, S.
Ursuegui, S. Erb, C. Michel, S. Kolodych, S. Cianférani and A.
Wagner, Bioconjugate Chem., 2017, 28, 1452–1457.
17 (a) G. S. Lal, G. P. Fez, R. J. Pesaresi and F. M. Prozonic, J.
Org. Chem., 1999, 64, 7048–7054; (b) C. Chen, C.-T. Chien
and C.-H. Su, J. Fluorine Chem., 2002, 115, 75–77; (c) J. M.
White, A. R. Tunoori, B. J. Turunen and G. I. Georg, J. Org.
Chem., 2004, 69, 2573–2576; (d) T. Gustafsson, R. Gilmour
and P. H. Seeberger, Chem. Commun., 2008, 26, 3022–3024;
(e) F. Beaulieu, L.-P. Beauregard, G. Courchesne, M.
Couturier, F. LaFlamme and A. L’Heureux, Org. Lett., 2009,
7
8
(a) A. Shibamoto, S. Sakaguchi and Y. Ishii, Tetrahedron Lett.,
2002, 43, 8859–8861; (b) N. Hirai, N. Sawatari, N. Nakamura,
S. Sakaguchi and Y. Ishii, J. Org. Chem., 2003, 68, 6587–
6590; (c) X. Baucherel, I. W. C. E. Arends, S. Ellwood and R.
A. Sheldon, Org. Process Res. Dev., 2003, 7, 426–428; (d) Y.
Kadoh, K. Oisaki and M. Kanai, Chem. Pharm. Bull., 2016, 64
737–753.
R. Amorati, M. Lucarini, V. Mugnaini, G. F. Pedulli, F.
Minisci, F. Recupero, F. Fontana, P. Astolfi and L. Greci, J.
Org. Chem., 2003, 68, 1747–1754.
,
11, 5050–5053; (f) J.-G. Kim and D. O. Jang, Synlett, 2010, 20
3049–3052; (g) G. M. Lee, R. Clément and R. T. Baker, Catal.
Sci. Technol., 2017, , 4996–5003; (h) T. Scattolin, K. Deckers
,
7
6 | J. Name., 2012, 00, 1-3
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