RSC Advances
Paper
1
3
Hz, 2H), 7.18–7.14 (m, 1H); C NMR (126 MHz, CDCl
3
) d 165.83,
3405; (e) E. Valeur and M. Bradley, Chem. Soc. Rev., 2009,
38, 606.
1
37.91, 134.97, 131.84, 129.09, 128.77, 127.03, 124.58, 120.24;
GC-MS (EI, 70 eV): m/z (%) ¼ 197 [M ] (43.6), 105 (100), 91 (6), 77
48), 65 (9), 51 (13.83).
+
4 (a) R. V. Kolakowski, N. Shangguan, R. R. Sauers and
L. J. Williams, J. Am. Chem. Soc., 2006, 128, 5695; (b)
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H. Heydt, Chem. Rev., 2015, 115, 2596; (f) Y. Wang,
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C. U. Maheswari, M. Venkateshwar and M. L. Kantam, Eur.
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Commun., 2012, 2427.
(
4
b
N,N-Dibenzylbenzamide (3k)
White solid; isolated yield: 95%; H NMR (400 MHz, CDCl
d 7.50–7.48 (m, 2H), 7.38–7.31 (m, 8H), 7.29 (t, J ¼ 7.0 Hz, 4H),
1
3
)
1
3
7
.13 (d, J ¼ 5.7 Hz, 2H), 4.70 (s, 2H), 4.39 (s, 2H); C NMR (101
MHz, CDCl ): d 172.26, 136.09, 129.65, 128.84, 128.71, 128.55,
3
1
(
(
28.39, 127.65, 127.51, 127.01, 126.68, 51.50, 46.81 ppm; GC-MS
+
EI, 70 eV): m/z (%) ¼ 301 [M ] (8.1), 210 (31.20), 105 (100), 91
16.40), 77 (30.32), 65 (5.96), 51 (4).
18a
N-Benzylbenzamide (3l)
1
White solid; isolated yield: 98%; H NMR (500 MHz, CDCl3)
5 (a) A. Brennfuhrer, H. Neumann and M. Beller, Angew.
Chem., Int. Ed., 2009, 48, 4133; (b) W. Magerlein,
A. M. Beller and F. Indolese, J. Mol. Catal. A: Chem., 2000,
156, 221; (c) J. S. Quesnel and B. A. Arndtsen, J. Am. Chem.
Soc., 2013, 135, 16841; (d) P. Xie, C. Xia and H. Huang, Org.
Lett., 2013, 15, 3370; (e) S. D. Friis, T. Skrydstrup and
S. L. Buchwald, Org. Lett., 2014, 16, 4296; (f) T. Xu and
H. Alper, J. Am. Chem. Soc., 2014, 136, 16970; (g)
J. R. Martinelli, T. P. Clark, D. A. Watson, R. H. Munday
and S. L. Buchwald, Angew. Chem., Int. Ed., 2007, 46, 8460;
(h) M. N. Burhardt, R. Taaning, N. C. Nielsen and
T. Skrydstrup, J. Org. Chem., 2012, 77, 5357; (i)
R. H. Munday, J. R. Martinelli and S. L. Buchwald, J. Am.
Chem. Soc., 2008, 130, 2754; (j) W. Han, F. Jin and Q. Zhou,
Synthesis, 2015, 47, 1861; (k) W. J. Ang, L.-C. Lo and
Y. Lam, Tetrahedron, 2014, 70, 8545; (l) H. Mei, J. Hu,
S. Xiao, Y. Lei and G. Li, Appl. Catal., A, 2014, 475, 40.
6 (a) K. Kumar, A. Zapf, D. Michalik, A. Tillack, T. Heinrich,
H. Bottcher, M. Arlt and M. Beller, Org. Lett., 2004, 6(1), 10;
(b) Y. Yamamoto, Adv. Synth. Catal., 2010, 352, 478.
d 7.80 (d, J ¼ 8.0 Hz, 2H), 7.49–7.23 (m, 8H), 6.67 (bs, 1H), 4.62
1
3
(
d, J ¼ 5.7 Hz, 2H); C NMR (126 MHz, CDCl
3
) d 167.44, 138.21,
1
2
34.34, 131.54, 128.76, 128.57, 127.88, 127.57, 126.99, 44.09,
9.71; GC-MS (EI, 70 eV): m/z (%) ¼ 211 [M ] (56), 210 (21), 106
+
(28), 105 (100), 91 (10), 77 (59), 51 (14).
Acknowledgements
The author R. S. Mane gratefully acknowledged the Council of
Scientic and Industrial Research (CSIR), India for providing
Senior Research Fellowship (SRF).
Notes and references
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94784 | RSC Adv., 2015, 5, 94776–94785
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