Communication
ChemComm
J. B. Henry, H. McNab and A. R. Mount, Chem. – Eur. J., 2009,
15, 5482; (e) J. Lv, Q. Liu, J. Tang, F. Perdih and K. Kranjc, Tetra-
hedron Lett., 2012, 53, 5248; ( f ) P. Kautny, D. Lumpi, Y. Wang,
A. Tissot, J. Bintinger, E. Horkel, B. Stoeger, C. Hametner, H. Hagemann,
D. Mab and J. Froehlich, J. Mater. Chem. C, 2014, 2, 2069.
8 Dehydrogenative route: A. W. Jones, M.-L. Louillat-Habermeyer and
F. W. Patureau, Adv. Synth. Catal., 2015, 357, 945.
Notes and references
1 For selected reviews, see: (a) W. Wu, Y. Liu and D. Zhu, Chem. Soc. Rev.,
2010, 39, 1489; (b) A. Narita, X.-Y. Wang, X. Feng and K. Muellen, Chem.
Soc. Rev., 2015, 44, 6616; (c) M. Stepien, E. Gonka, M. Zyla and N. Sprutta,
Chem. Rev., 2017, 117, 3479; (d) M. Krzeszewski, D. Gryko and D. T. Gryko,
´
Acc. Chem. Res., 2017, 50, 2334; (e) H. Zhylitskaya and M. St˛epien, Org.
Chem. Front., 2018, 5, 2395; ( f ) T. Janosik, A. Rannug, U. Rannug,
9 Scholl-type/Mallory-type reactions, see for example: (a) M. Grzybowski,
K. Skonieczny, H. Butenschoen and D. T. Gryko, Angew. Chem., Int. Ed.,
2013, 52, 9900; (b) F. B. Mallory and C. W. Mallory, Org. React., 1984, 30, 1;
(c) W. H. Laarhoven, Org. Photochem., 1989, 10, 163; (d) H. Meier, Angew.
Chem., Int. Ed. Engl., 1992, 31, 1399; (e) Y. Tominaga and R. N. J. Castle,
Heterocycl. Chem., 1996, 33, 523; ( f ) S. Hagen and H. Hopf, Top. Curr.
Chem., 1998, 196, 45; (g) K. B. Jørgensen, Molecules, 2010, 15, 4334.
10 Methods of Quantum Chemical Calculations: Input structures for
the compounds were generated by applying the universal force field
(UFF)11 implemented in the Avogadro program.12 We performed
structure optimization in Gaussian 0913 with the (TD)-DFT func-
tional B3LYP as implemented in Turbomole 7.314 by addition of
Grimme’s dispersion correction D3.15 The def2-TZVP basis set was
used for all elements. Optimized structures were tested for mini-
mum geometry by application of frequency calculations. No ima-
ginary frequencies were found. The scaling factors 0.956 (CH
stretching modes) and 0.97 (fingerprint) were used. To calculate
the vertical electronic transitions, TD-DFT was used with the pre-
viously mentioned functional and basis set.
¨
¨
N. Wahlstrom, J. Slatt and J. Bergman, Chem. Rev., 2018, 118, 9058.
2 (a) T. Ishisone, S. Seo, Y. Nonaka, T. Kawata and N. Ohsawa, J. Soc.
Inf. Disp., 2014, 22, 404; (b) S. Y. Moon, B. S. Lee, S. H. Lee, G. M. Lee,
D. H. Choi, D. H. Kim and J. H. Park, Preparation of carbazoles for
organic electronic element, KR Pat., 2013106255, 2013; (c) H. Suzuki,
S. Seo, S. Kawakami and T. Suzuki, Dibenzo[c,g]carbazole compounds,
light-emitting components, light-emitting devices, display devices, lighting
devices and electronic devices, US Pat., 20130020561, 2013; (d) X. Pu,
M. Zhang, J. Lan, S. Chen, Z. Liu, W. Liang, Y. Yang, M. Zhang and
J. You, Org. Lett., 2019, 14, 1139.
3 (a) W. Matsuoka, H. Ito and K. Itami, Angew. Chem., Int. Ed., 2017,
56, 12224; (b) H. Kitano, W. Matsuoka, H. Ito and K. Itami, Chem.
Sci., 2018, 9, 7556.
4 For some selected reviews, see: (a) C.-L. Sun, B.-J. Li and Z.-J. Shi,
Chem. Commun., 2010, 46, 677; (b) C. S. Yeung and V. M. Dong, Chem.
Rev., 2011, 111, 1215; (c) L. McMurray, F. O’Hara and M. J. Gaunt,
Chem. Soc. Rev., 2011, 40, 1885; (d) P. B. Arockiam, C. Bruneau and
P. H. Dixneuf, Chem. Rev., 2012, 112, 5879; (e) J. Yamaguchi, A. D.
Yamaguchi and K. Itami, Angew. Chem., Int. Ed., 2012, 51, 8960;
( f ) S. I. Kozhushkov and L. Ackermann, Chem. Sci., 2013, 4, 886;
(g) C. Liu, J. Yuan, M. Gao, S. Tang, W. Li, R. Shi and A. Lei, Chem.
Rev., 2015, 115, 12138; (h) T. Gensch, M. N. Hopkinson, F. Glorius and
J. Wencel-Delord, Chem. Soc. Rev., 2016, 45, 2900; (i) Y. Qin, L. Zhu
and S. Luo, Chem. Rev., 2017, 117, 9433; ( j) D.-S. Kim, W.-J. Park and
C.-H. Jun, Chem. Rev., 2017, 117, 8977.
5 Early studies on the direct oxidation of N-phenyl-2-napthylamine:
(a) J. Rehner Jr., F. W. Banes and S. B. Robison, J. Am. Chem. Soc.,
1945, 67, 605; (b) D. F. Bowman, B. S. Middleton and K. U. Ingold,
J. Org. Chem., 1969, 34, 3456; (c) M. Smrcina, S. Vyskocil, B. Maca,
M. Polasek, T. A. Claxton, A. P. Abbott and P. Kocovsky, J. Org.
Chem., 1994, 59, 2156. For related works, see: (d) K. Nakano,
Y. Hidehira, K. Takahashi, T. Hiyama and K. Nozaki, Angew. Chem.,
Int. Ed., 2005, 44, 7136; (e) N. Ogawa, Y. Yamaoka, H. Takikawa,
K. Tsubaki and K. Takasu, J. Org. Chem., 2018, 83, 7994.
11 A. K. Rappe, C. J. Casewit, K. S. Colwell, W. A. Goddard and
W. M. Skiff, J. Am. Chem. Soc., 1992, 114, 10024.
12 M. D. Hanwell, D. E. Curtis, D. C. Lonie, T. Vandermeersch, E. Zurek
and G. R. Hutchison, J. Cheminf., 2012, 4, 17.
13 M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb,
J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji,
X. Li, M. Caricato, A. Marenich, J. Bloino, B. G. Janesko, R. Gomperts,
B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg,
D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng,
A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao,
N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota,
R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao,
H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery Jr., J. E. Peralta,
F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin,
V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari,
A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam,
M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin,
K. Morokuma, O. Farkas, J. B. Foresman and D. J. Fox, Gaussian 09,
Revision A.02, Gaussian, Inc., Wallingford, CT, 2016.
6 K. Goto, R. Yamaguchi, S. Hiroto, H. Ueno, T. Kawai and H. Shinokubo,
Angew. Chem., Int. Ed., 2012, 51, 10333.
7 Pre-activated route: (a) H. G. Dunlop and S. H. Tucker, J. Chem. Soc.,
¨
1939, 1945; (b) C. Niebel, V. Lokshin, A. Ben-Asuly, W. Marine, 14 F. Furche, R. Ahlrichs, C. Hattig, W. Klopper, M. Sierka and
A. Karapetyanac and V. Khodorkovsky, New J. Chem., 2010, 34, 1243;
F. Weigend, Wiley Interdiscip. Rev.: Comput. Mol. Sci., 2014, 4, 91.
(c) M. Rivoal, L. Bekere, D. Gachet, V. Lokshin, W. Marine and 15 S. Grimme, J. Antony, S. Ehrlich and H. Krieg, J. Chem. Phys., 2010,
V. Khodorkovsky, Tetrahedron, 2013, 69, 3302; (d) S. I. Wharton, 132, 154104.
13752 | Chem. Commun., 2019, 55, 13749--13752
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