Please do not adjust margins
ChemComm
Page 4 of 5
COMMUNICATION
Journal Name
3
DOI: 10.1039/C9CC05178C
Belitz and L. J. Gooßen, Angew. Chem. Int. Ed., 2016, 55,
14752; (c) C. W. Liu, Z. X. Qin, C. L. Ji, X. Hong and M. Szostak,
Chem. Sci., 2019, 10, 5736; (d) D. M. Pichette and L. J.
Gooßen, Chem. Eur. J., 2016, 22, 18654; (e) J. Tang, D.
Hackenberger and L. J. Gooßen, Angew. Chem. Int. Ed., 2016,
55, 11296; (f) D. M. Pichette and L. J. Gooßen, Chem. Eur. J.,
2016, 22, 18654; (g) A. Biafora, B. A. Khan, J. Bahri, J. M.
Hewer and L. J. Goossen, Org. Lett., 2017, 19, 1232. (h) M.
Font, J. M. Quibell, G. J. P. Perry and I. Larrosa, Chem.
Commun. 2017, 53, 5584.
(a) E. Kudo, Y. Shibata, M. Yamazaki, K. Masutomi, Y.
Miyauchi, M. Fukui, H. Sugiyama, H. Uekusa, T. Satoh, M.
Miura and K. Tanaka, Chem. Eur. J., 2016, 22, 14190; (b) G.
Liu, G. Kuang, X. Zhang and N. Lu, Org. Lett., 2019, 21, 3043;
(c) X. Liu, H. Gao, S. Zhang, Q. Li and H. Wang, ACS Catal.,
2017, 7, 5078; (d) Y. Qiu, C. Tian, L. Massignan, T. Rogge, L.
and Ackermann, Angew. Chem. Int. Ed., 2018, 57, 5818; (e) S.
Yedage and B. Bhanage, Green Chem., 2016, 18, 5635; (f) K.
Ueura, T. Satoh and M. Miura, J. Org. Chem., 2007, 72, 5362.
(a) Y. Park, S. Jee, J. G. Kim and S. Chang, Org. Process Res.
Dev., 2015, 19, 1024; (b) Y. Park, K. T. Park, J. G. Kim and S.
Chang, J. Am. Chem. Soc., 2015, 137, 4534; (c) H. Wang, G. D.
Tang and X. W. Li, Angew. Chem., Int. Ed., 2015, 54, 13049;
(d) H. Wang, G. Tang and X. W. Li, Angew. Chem. Int. Ed.,
2015, 54, 13049; (e) Y. Park, J. Heo, M. H. Baik and S. Chang,
J. Am. Chem. Soc., 2016, 138, 14020; (f) Q. Ma, S. Lv, J. Li, C.
Zhang, L. Hai, Q. Wang and Y. Wu, Org. Chem. Front., 2017,
4, 2184.
4
5
Figure 1. a) Normalized absorption and PL spectra of 3a. b)
Fluorescence photographs of 3a with 0% and 99% water. c) Emission
spectra of 3a in THF/water mixtures. d) Plots of emission intensity I/I0
(407 nm, black line) and wavelength (red line) of 3a in different water
fractions. (λex= 372 nm, concentration: 10 µM).
conformation in solid state.
In conclusion, an efficient and practical Rh(III)-catalyzed
amidation of benzoic acids with dioxazolones has been
developed to afford diverse benzoxazinones. The application
of carboxylic acid as a functionalizable directing group was
successfully expanded in the regioselective amination wherein
carboxylic acid directed twice the amidation reactions prior to
the annulation to afford 2,5-benzoxazinones. A directed
selective single amidation was also observed to deliver 2-
6
7
(a) G. N. Hermann and C. Bolm, ACS Catal. 2017, 7, 4592. (b)
J. Park and Chang, S. Angew. Chem. Int. Ed., 2015, 54, 14103;
(c) J. Park, J. Lee and S. Chang, Angew. Chem. Int. Ed., 2017,
56, 4256; (d) J. Ding, W. Jiang, H. Y. Bai, T. M. Ding, D. Gao, X.
Bao and S. Y. Zhang, Chem. Commun., 2018, 54, 8889; (e) S.
S. Bera, M. R. Sk and M. S. Maji, Chem. Eur. J., 2019, 25, 1806.
(a) H. Deng, H. Li, W. Zhang and L. Wang, Chem. Commun.,
2017, 53, 10322; (b) C. Liu, M. Liu, J. Sun, C. Li and L. Dong,
Org. Chem. Front., 2018, 5, 2115; (c) A. E. Hande, V. B.
Ramesh and K. R. Prabhu, Chem. Commun. 2018, 54, 12113;
(d) H. Xiong, S. Xu, S. Sun and J. Cheng, Org. Chem. Front.,
2018, 5, 2880. (e) J. Wang, S. Zha, K. Chen, F. Zhang, C. Song
and J. Zhu, Org, Lett., 2016, 18, 2062; (f) P. Chirila, L.
Skibinski, K. Miller, A. Hamilton and C. Whiteoak, Adv. Synth.
Catal., 2018, 360, 2324; (g) F. Wang, L. Jin, L. Kong and X. Li,
Org. Lett., 2017, 19, 1812; (h) Q. Wang, F. Wang, X. Yang, X.
Zhou and X. Li, Org. Lett., 2016, 18, 6144; (i) F. Wang, H.
Wang, Q. Wang, S. Yu and X. Li, Org. Lett., 2016, 18, 1306;
Y. Hwang, Y. Park and S. Chang, Chem. Eur. J., 2017, 23,
11147.
(a) A. V. Lygin and A. de Meijere, J. Org. Chem., 2009, 74,
4554; (b) Z. Y. Ge, Q. M. Xu, X. D. Fei, T. Tang, Y. M. Zhu, S. J.
Ji, J. Org. Chem., 2013, 78, 4524; (c) K. Proisl, S. Kafka, D.
Urankar, M. Gazvoda, R. Kimmel, J. Kosmrlj, Org. Biomol.
Chem., 2014, 12, 9650; (d) Y. C. Zhang, Z. P. Yin, H. Wang and
X. F. Wu, Org. Lett., 2019, 21, 3242; (e) M. Lang and J. Wang,
Org. Chem. Front., 2019, 6, 1367; (f) M. Pattarawarapan, S.
Wet-osot, D. Yamano and W. Phakhodee, Synlett, 2017, 28,
589.
benzoxazinones,
a
process exclusively driven by the
dimethylamino group-substituted dioxazolones with strong
electron-donating property. The mechanisms underlying these
reactions were investigated and the catalytic pathways were
proposed. Interestingly, 2,5-substitued benzoxazinones
displayed prominent AIE properties with ESIPT phenomenon
that can be utilized in various fields.
This work was supported by the National Key R&D Program of
China (No. 2017YFE0102200) and the National Natural Science
Foundation of China (No. 21472170).
8
9
Conflicts of interest
There are no conflicts to declare.
References
1
(a) Y. Park, Y. Kim and S. Chang, Chem. Rev., 2017, 117, 9247;
(b) M. Gulías and J. L. Mascareñas, Angew. Chem. Int. Ed.,
2016, 55, 11000; (c) D. S. Kim, W. J. Park and C. H. Jun, Chem.
Rev., 2017, 117, 8977; (d) C. Sambiagio, D. Schonbauer, R.
Blieck, T. Dao-Huy, G. Pototschnig, P. Schaaf, T. Wiesinger,
M. F. Zia, J. Wencel-Delord, T. Besset, B. U. W. Maes and M.
Schnurch, Chem. Soc. Rev., 2018, 47, 6603.
(a) F. Zhang and D. R. Spring, Chem. Soc. Rev., 2014, 43,
6906; (b) S. Rej, Angew. Chem. Int. Ed., 2018, 58, 2; (b) G.
Rousseau and B. Breit, Angew. Chem. Int. Ed., 2011, 50,
2450.
10 (a) V. S. Padalkar and S. Seki, Chem. Soc. Rev., 2016, 45, 169;
(b) A. C. Sedgwick, L. Wu, H. H. Han, S. D. Bull, X. P. He, T. D.
James, J. L. Sessler, B. Z. Tang, H. Tian and J. Yoon, Chem.
Soc. Rev., 2018, 47, 8842.
2
4 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins