F
Synlett
G.-W. Zhang et al.
Letter
Baidya, M. Chem. Eur. J. 2016, 22, 1592. (h) Ji, D.; He, X.; Xu, Y.;
Xu, Z.; Bian, Y.; Liu, W.; Zhu, Q.; Xu, Y. Org. Lett. 2016, 18, 4478.
(10) CCDC 1565719 contains the supplementary crystallographic
data for compound 3ag. The data can be obtained free of charge
from The Cambridge Crystallographic Data Centre via
www.ccdc.cam.ac.uk/getstructures.
(11) Sahoo, H.; Mukherjee, S.; Grandhi, G. S.; Selvakumar, J.; Baidya,
M. J. Org. Chem. 2017, 82, 2764.
(i) Guo, H.; Chen, M.; Jiang, P.; Chen, J.; Pan, L.; Wang, M.; Xie, C.;
Zhang, Y. Tetrahedron 2015, 71, 70. (j) Jin, L.-K.; Lu, G.-P.; Cai, C.
Org. Chem. Front. 2016, 3, 1309. (k) He, X.; Xu, Y.-Z.; Kong, L.;
Wu, H.; Ji, D.; Wang, Z.; Xu, Y.; Zhu, Q. Org. Chem. Front. 2017, 4,
1
046. (l) Zhao, L.; Li, P.; Xie, X.; Wang, L. Org. Chem. Front. 2018,
(12) N-Aryl-N-quinolin-8-ylaroylamides 3aa–3ma; General Pro-
cedure
5, 1689.
(
(
(
(
(
4) Suess, A. M.; Ertem, M. Z.; Cramer, C. J.; Stahl, S. S. J. Am. Chem.
An oven-dried Schlenk tube (10 mL) equipped with a magnetic
stirrer bar was charged with the appropriate N-quinolin-8-
ylaroylamide 1 (0.3 mmol), diaryliodonium hexafluorophos-
Soc. 2013, 135, 9797.
5) Kathiravan, S.; Ghosh, S.; Hogarth, G.; Nicholls, I. A. Chem.
Commun. 2015, 51, 4834.
.
phate 2 (0.6 mmol), Cu(OAc) H O (20 mol%, 0.06 mmol), and 4
2
2
6) Xiao, Z.; Yue, Q.; Ran, Z.; Zhang, Q.; Li, D. Youji Huaxue 2018, 83,
Å MS (40 mg). DCE (3.0 mL) was then added from a syringe, and
1193.
the mixture was stirred for 48 h at 80 °C in air. H O (6 mL) was
2
7) Peng, Y.; Lei, J.; Qiu, R.; Peng, L.; Au, C.-T.; Yin, S.-F. Org. Biomol.
Chem. 2018, 16, 4065.
8) For a recent review, see: (a) Yosimura, A.; Zhdankin, V. V. Chem.
Rev. 2016, 116, 3328. (b) Aradi, K.; Tóth, B. L.; Tolnai, G. L.;
Novák, Z. Synlett 2016, 27, 1456. (c) Olofsson, B. Top. Curr. Chem.
added to quench the reaction, and the resulting mixture was
extracted with EtOAc (×2). The combined organic extracts were
washed with brine, dried (Na SO ), and concentrated. The crude
2
4
product was purified by flash column chromatography [silica
gel, PE–EtOAc (3:1)].
2016, 373, 135. (d) Merritt, E. A.; Olofsson, B. Angew. Chem. Int.
N-Phenyl-N-quinolin-8-ylbenzamide (3aa)
Ed. 2009, 48, 9052.
9) (a) Sandtorv, A. H.; Stuart, D. R. Angew. Chem. Int. Ed. 2016, 55,
Colorless solid; yield: 71 mg (73%); mp 125–128 °C. IR (KBr):
3054, 1660, 1594, 1493, 1463, 1343, 1310, 1269, 1177, 1132,
(
–1
1
15812. (b) Tinnis, F.; Stridfeldt, E.; Lundberg, H.; Adolfsson, H.;
1075, 1028, 825, 789, 700 cm . H NMR (400 MHz, CDCl ):
3
Olofsson, B. Org. Lett. 2015, 17, 2688. (c) Jung, S.-H.; Sung, D.-B.;
Park, C.-H.; Kim, W.-S. J. Org. Chem. 2016, 81, 7717.
δ = 8.89–8.91 (m, 1 H), 8.07–8.09 (m, 1 H), 7.70–7.72 (m, 1 H),
7.57–7.62 (m, 3 H), 7.45–7.49 (m, 1 H), 7.32–7.35 (m, 1 H),
13
(d) Lucchetti, N.; Scalone, M.; Fantasia, S.; Muñiz, K. Angew.
7.22–7.24 (m, 4 H), 7.09–7.16 (m, 4 H). C NMR (100 MHz,
Chem. Int. Ed. 2016, 55, 13335. (e) Li, P.; Weng, Y.; Xu, X.; Cui, X.
J. Org. Chem. 2016, 81, 3994. (f) Aradi, K.; Mészáros, Á.; Tóth, B.
L.; Vincze, Z.; Novák, Z. J. Org. Chem. 2017, 82, 11752.
CDCl ): δ = 171.6, 150.7, 144.7, 144.4, 141.8, 136.8, 135.8, 129.7,
3
129.3, 129.2, 128.9, 128.7, 127.6, 127.4, 126.9, 126.3, 125.8,
+
121.6. HRMS (ESI): m/z [M
25.13354; found: 325.13327.
+
H] calcd for C22H17N O:
2
3
©
Georg Thieme Verlag Stuttgart · New York — Synlett 2018, 29, A–F