H
S. Giofrè et al.
Paper
Synthesis
13C NMR (126 MHz, CDCl3): = 151.3 (s), 144.7 (s), 138.4 (s), 136.2 (s),
135.2 (d), 129.5 (d), 129.0 (d), 128.6 (d), 124.4 (d), 119.4 (t), 118.7 (d),
55.8 (d), 49.2 (t), 21.7 (q).
Almendros, P.; Rodriguez-Acebes, R. J. Org. Chem. 2006, 71,
2346. (k) Beccalli, E. M.; Bernasconi, A.; Borsini, E.; Broggini, G.;
Rigamonti, M.; Zecchi, G. J. Org. Chem. 2010, 75, 6923.
(3) (a) Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S.
Chem. Rev. 2007, 107, 5318. (b) Chen, X.; Engle, K. M.; Wang, D.-
H.; Yu, J.-Q. Angew. Chem. Int. Ed. 2009, 48, 5094. (c) Beccalli, E.
M.; Broggini, G.; Gazzola, S.; Mazza, A. Org. Biomol. Chem. 2014,
12, 6767.
(4) (a) Yin, G.; Wu, T.; Liu, G. Chem. Eur. J. 2012, 18, 451. (b) Zhu, H.;
Chen, P.; Liu, G. Org. Lett. 2015, 17, 1485. (c) Zhu, H.; Chen, P.;
Liu, G. J. Am. Chem. Soc. 2014, 136, 1766. (d) Yin, G.; Liu, G.
Angew. Chem. Int. Ed. 2008, 47, 5442.
(5) (a) Broggini, G.; Barbera, V.; Beccalli, E. M.; Chiacchio, U.;
Fasana, A.; Galli, S.; Gazzola, S. Adv. Synth. Catal. 2013, 355,
1640. (b) Broggini, G.; Beccalli, E. M.; Borelli, T.; Brusa, F.;
Gazzola, S.; Mazza, A. Eur. J. Org. Chem. 2015, 4261.
(6) Gazzola, S.; Beccalli, E. M.; Borelli, T.; Castellano, C.; Diamante,
D.; Broggini, G. Synlett 2018, 29, 503.
MS: m/z = 365.22 [M + Na]+.
1,4-Diphenyl-3-(p-tolyl)-1,3-diazepan-2-one (9)
Colorless oil; yield: 51 mg (57%); Rf = 0.37 (hexane/EtOAc, 3:1).
IR: 1694 cm–1
.
1H NMR (300 MHz, CDCl3): = 7.62–7.11 (m, 12 H), 7.05 (d, J = 8.4 Hz,
2 H), 4.93 (dd, J = 8.1, 6.2 Hz, 1 H), 3.82 (td, J = 7.3, 2.0 Hz, 2 H), 2.28 (s,
3 H), 2.24–2.02 (m, 2 H), 1.90–1.49 (m, 2 H).
13C NMR (75 MHz, CDCl3): = 154.4 (s), 141.7 (s), 141.1 (s), 136.2 (s),
132.5 (s), 130.4 (d), 129.3 (d), 128.7 (d), 128.6 (d), 128.3 (d), 128.2 (d),
126.9 (d), 119.5 (d), 63.4 (d), 48.3 (t), 37.1 (t), 26.0 (t), 20.7 (q).
MS: m/z = 379.81 [M + Na]+.
Anal. Calcd C24H24N2O: C, 80.86; H, 6.79; N, 7.86. Found: C, 81.07; H,
6.70; N, 7.79.
(7) (a) Wang, Z.; Luo, W.; Lu, L.; Yin, B. J. Org. Chem. 2018, 83,
10080. (b) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Ghirga, F.;
Goggiamani, A.; Iazzetti, A.; Marinelli, F. Synthesis 2018, 50,
1133. (c) Yang, M.-N.; Yan, D.-M.; Zhao, Q.-Q.; Chen, J.-R.; Xiao,
W.-J. Org. Lett. 2017, 19, 5208. (d) Wu, L.; Meng, Y.; Ferguson, J.;
Wang, L.; Zeng, F. J. Org. Chem. 2017, 82, 4121. (e) Yu, R.; Li, D.;
Zeng, F. J. Org. Chem. 2018, 83, 323. (f) Zhang, W.; Chen, P.; Liu,
G. Angew. Chem. Int. Ed. 2017, 56, 5336. (g) Bao, X.; Wang, Q.;
Zhu, J. Angew. Chem. Int. Ed. 2017, 56, 9577. (h) Yang, H.-B.;
Pathipati, S. R.; Selander, N. ACS Catal. 2017, 7, 8441. (i) Zheng,
J.; Huang, L.; Huang, C.; Wu, W.; Jiang, H. J. Org. Chem. 2015, 80,
1235. (j) Faulkner, A.; Scott, J. S.; Bower, J. F. J. Am. Chem. Soc.
2015, 137, 7224. (k) Bao, H.; Bayeh, L.; Tambar, U. K. Chem. Sci.
2014, 5, 4863. (l) Hewitt, J. F. M.; Williams, L.; Aggarwal, P.;
Smith, C. D.; France, D. J. Chem. Sci. 2013, 4, 3538. (m) Schultz, D.
M.; Wolfe, J. P. Synthesis 2012, 44, 351. (n) Jiang, C.; Covell, D. J.;
Stepan, A. F.; Plummer, M. S.; White, M. C. Org. Lett. 2012, 14,
1386. (o) Brenzovich, W. E. Jr.; Benitez, D.; Lackner, A. D.;
Shunatona, H. P.; Tkatchouk, E.; Goddard, W. A. III.; Toste, F. D.
Angew. Chem. Int. Ed. 2010, 49, 5519. (p) Fritz, J. A.; Wolfe, J. P.
Tetrahedron 2008, 64, 6838. (q) Tamaru, Y.; Hojo, M.;
Kawamura, S.; Yoshida, Z. J. Org. Chem. 1986, 51, 4089.
(r) Zhang, L.; Dong, C.; Ding, C.; Chen, J.; Tang, W.; Li, H.; Xu, L.;
Xiao, J. Adv. Synth. Catal. 2013, 355, 1570. (s) Trejos, A.; Fardost,
A.; Yahiaoui, S.; Larhed, M. Chem. Commun. 2009, 7587.
(8) (a) Rao, W.-H.; Yin, X.-S.; Shi, B.-F. Org. Lett. 2015, 17, 3758.
(b) Gazzola, S.; Beccalli, E. M.; Borelli, T.; Castellano, C.;
Chiacchio, M. A.; Diamante, D.; Broggini, G. J. Org. Chem. 2015,
80, 7226. (c) Strambeanu, I. I.; White, M. C. J. Am. Chem. Soc.
2013, 137, 12032. (d) Muniz, K.; Iglesias, A.; Fang, Y. Chem.
Commun. 2009, 5591. (e) Gimeno, A.; Cuenca, A. B.; Médio-
Simon, M.; Asensio, G. Adv. Synth Catal. 2014, 356, 229. (f) Li, H.;
Widenhoefer, A. Tetrahedron 2010, 66, 4827. (g) Cochran, B. M.;
Micheal, F. E. Org. Lett. 2008, 10, 5039.
(9) (a) Rahbæk, L.; Christophersen, C. J. Nat. Prod. 1997, 60, 175.
(b) Sheppeck, J. E. II.; Gilmore, J. L.; Tebben, A.; Xue, C.-B.; Liu,
R.-Q.; Decicco, C. P.; Duan, J. J.-W. Bioorg. Med. Chem. Lett. 2007,
17, 2769. (c) Batra, S.; Tusi, Z.; Madapa, S. Anti-Infective Agents
Med. Chem. 2006, 5, 135. (d) Bronson, J. J.; DenBleyker, K. L.;
Falk, P. L.; Mate, R. A.; Ho, H.-T.; Pucci, M. J.; Snyder, L. B. Bioorg.
Med. Chem. Lett. 2003, 13, 873. (e) Congiu, C.; Cocco, M. T.;
Onnis, V. Bioorg. Med. Chem. Lett. 2008, 18, 989. (f) Watanabe,
K.; Morinaka, Y.; Hayashi, Y.; Shinoda, M.; Nishi, H.; Fukushima,
Funding Information
Università degli Studi di Milano is acknowledged for financial sup-
port. Support from European Cooperation in Science and Technology
through CMST COST Action [CA15106 - C–H Activation in Organic
Synthesis (CHAOS)] is also gratefully acknowledged.
E
uro
p
e
a
n
C
o
o
p
erati
o
ni
n
S
c
i
e
n
c
e
a
n
d
T
e
c
h
n
o
l
o
g
y
(C
A
1
5
1
0
6)
Supporting Information
Supporting information for this article is available online at
S
u
p
p
orti
n
gInformati
o
n
S
u
p
p
orit
n
gInformati
o
n
References
(1) (a) Tietze, L. F. Chem. Rev. 1996, 96, 115. (b) Poli, G.;
Giambastiani, G.; Heumann, A. Tetrahedron 2000, 56, 5959.
(c) Pellissier, H. Chem. Rev. 2013, 113, 442. (d) Clavier, H.;
Pellissier, H. Adv. Synth. Catal. 2012, 354, 3347. (e) Yin, G.; Mu,
X.; Liu, G. Acc. Chem. Res. 2016, 49, 2413. (f) Vlaar, T.; Ruijter, E.;
Orru, V. A. Adv. Synth. Catal. 2011, 353, 809. (g) Jensen, K. H.;
Sigman, M. S. Org. Biomol. Chem. 2008, 6, 4083.
(2) For selected examples of intramolecular oxidative Pd-catalyzed
domino reactions on alkenes, see: (a) Chen, P.-Y.; Huang, K.-S.;
Tsai, C.-C.; Wang, T.-P.; Wang, E.-C. Org. Lett. 2012, 14, 4930.
(b) Alonso, F.; Sanchez, D.; Soler, T.; Yus, M. Adv. Synth. Catal.
2008, 350, 2118. (c) Abbiati, G.; Beccalli, E. M.; Broggini, G.;
Martinelli, M.; Paladino, G. Synlett 2006, 73. (d) Szolcsanyi, P.;
Gracza, T. Chem. Commun. 2005, 3948. (e) Alladoum, J.;
Vrancken, E.; Mangeney, P.; Roland, S.; Kadouri-Puchot, C. Org.
Lett. 2009, 11, 3746. For selected examples of analogous reac-
tions on alkynes, see: (f) Asao, N.; Chan, C. S.; Takahashi, K.;
Yamamoto, Y. Tetrahedron 2005, 61, 11322. (g) Watanabe, K.;
Iwata, Y.; Adachi, S.; Nishikawa, T.; Yoshida, Y.; Kameda, S.; Ide,
M.; Saikawa, Y.; Nakata, M. J. Org. Chem. 2010, 75, 5573. For
selected examples of analogous reactions on allenes, see:
(h) Gazzola, S.; Beccalli, E. M.; Bernasconi, A.; Borelli, T.;
Broggini, G.; Mazza, A. Eur. J. Org. Chem. 2016, 4534. (i) Le Bras,
J.; Muzart, J. Chem. Soc. Rev. 2014, 43, 3003. (j) Alcaide, B.;
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2019, 51, A–I