The Journal of Organic Chemistry
Note
δ 7.80 (d, J = 7.9 Hz, 2H), 7.57−7.63 (m, 3H), 7.47 (t, J = 7.7 Hz,
2H), 7.34−7.40 (m, 2H), 2.42 (s, 3H); 13C NMR (151 MHz, CDCl3)
δ 196.9, 138.1, 137.7, 137.6, 133.1, 132.3, 130.4, 130.0, 128.2, 128.1,
127.3, 21.4; mp 155−158 °C (lit.31k mp 159−160 °C).
2-Naphthaldehyde (4f).27 Following general procedure A,
colorless liquid (42%, 16.4 mg): 1H NMR (400 MHz, CDCl3) δ
10.16 (s, 1H), 8.33 (s, 1H), 8.01−7.89 (m, 4H), 7.66−7.57 (m, 2H);
13C NMR (101 MHz, CDCl3) δ 192.3, 136.4, 134.6, 134.1, 132.6,
129.5, 129.1, 129.0, 128.1, 127.1, 122.7.
Phenyl(2,3,4-trifluorophenyl)methanone (2n). Following gen-
1
Benzaldehyde (6a).28 Following general procedure A, colorless
liquid (42%, 22.3 mg): 1H NMR (600 MHz, CDCl3) δ 10.01 (s, 1H),
7.87 (dd, J = 8.1, 1.1 Hz, 2H), 7.65−7.59 (m, 1H), 7.52 (t, J = 7.6 Hz,
2H); 13C NMR (101 MHz, CDCl3) δ 192.3, 136.4, 134.4, 129.7,
129.0.
eral procedure A, pale yellow liquid (55%, 33 mg): H NMR (400
MHz, CDCl3) δ 7.85−7.75 (m, 2H), 7.67−7.60 (m, 1H), 7.54−7.46
(m, 2H), 7.39−7.29 (m, 1H), 7.11 (m, 1H); 13C NMR (101 MHz,
CDCl3) δ 191.1, 153.2 (ddd, J = 255.8, 10.1, 3.1 Hz), 149.8 (ddd, J =
257.1, 10.8, 3.7 Hz), 140.0 (dt, J = 254.2, 15.4 Hz), 136.9, 133.9, 129.7
(t, J = 7.6 Hz), 128.7, 125.9, 124.9 (ddd, J = 8.2, 4.6, 3.3 Hz), 112.67
(dd, J = 17.8, 3.8 Hz); 19F NMR (377 MHz, CDCl3) δ −128.4 (dd, J =
20.2, 10.4 Hz), −131.6 (dd, J = 21.3, 10.4 Hz), −158.9 (t, J = 20.7
Hz); HRMS calcd for C13H7F3O (M+) 236.0449, found 236.0450.
Naphthalen-2-yl(phenyl)methanone (2o).20 Following general
procedure A, white solid (85%, 49 mg): 1H NMR (400 MHz, CDCl3)
δ 8.26 (s, 1H), 7.97−7.83 (m, 6H), 7.65−7.58 (m, 2H), 7.57−7.47 (m,
3H); 13C NMR (151 MHz, CDCl3) δ 196.7, 137.9, 135.2, 134.8,
132.3, 132.2 131.8, 130.1, 129.4, 128.4−128.1 (m), 127.8, 126.8,
125.8; mp 81−83 °C (lit.31l mp 80−81 °C).
1-(1-Phenylvinyl)-4-vinylbenzene (7a): colorless liquid; 1H
NMR (600 MHz, CDCl3) δ 7.42 (d, J = 8.2 Hz, 2H), 7.37 (dd, J =
15.5, 6.9 Hz, 7H), 6.77 (dd, J = 17.6, 10.9 Hz, 1H), 5.81 (d, J = 17.6
Hz, 1H), 5.50 (d, J = 17.8 Hz, 3H), 5.30 (d, J = 10.9 Hz, 1H); 13C
NMR (151 MHz, CDCl3) δ 149.7, 141.4, 140.9, 137.0, 136.4, 128.5,
128.3, 128.2, 127.7, 126.0, 114.2, 113.9. HRMS calcd for C16H14 (M+)
206.1096, found 206.1098.
Phenyl(4-vinylphenyl)methanone (7b).29 Following general
procedure A, colorless liquid (42.6%, 88.6 mg, 24 h) (41.3%, 85.9
mg, 48 h): 1H NMR (600 MHz, CDCl3) δ 7.88−7.71 (m, 4H), 7.64−
7.56 (m, 1H), 7.54−7.44 (m, 4H), 6.78 (dd, J = 17.6, 10.9 Hz, 1H),
5.89 (d, J = 17.6 Hz, 1H), 5.40 (d, J = 10.9 Hz, 1H); 13C NMR (151
MHz, CDCl3) δ 196.2, 141.5, 137.8, 136.7, 136.0, 132.3, 130.5, 129.9,
128.2, 126.0, 116.6.
9H-Fluoren-9-one (2p).21 Following general procedure A, pale
yellow solid (61%, 28 mg): 1H NMR (400 MHz, CDCl3) δ 7.65 (d, J
= 7.3 Hz, 2H), 7.52−7.46 (m, 4H), 7.29 (t, J = 7.2 Hz, 2H); 13C NMR
(101 MHz, CDCl3) δ 193.9, 144.4, 134.7, 134.1, 129.0, 124.3, 120.3;
mp 81−83 °C (lit.31m mp 83−85 °C).
4-(1-Phenylvinyl)benzaldehyde (7c).30 Following general pro-
9H-Thioxanthen-9-one (2q).22 Following general procedure A,
1
cedure A, colorless liquid (21.3%, 44.7 mg, 24 h): H NMR (600
1
pale yellow solid (56%, 30 mg): H NMR (400 MHz, CDCl3) δ 8.63
MHz, CDCl3) δ 10.02 (s, 1H), 7.85 (d, J = 8.2 Hz, 2H), 7.50 (d, J =
8.1 Hz, 2H), 7.35 (d, J = 5.3 Hz, 3H), 7.32−7.28 (m, 2H), 5.58 (d, J =
6.9 Hz, 2H); 13C NMR (151 MHz, CDCl3) δ 191.8, 149.2, 147.6,
140.6, 135.6, 129.7, 128.8, 128.4, 128.2, 128.1, 116.5.
(dd, J = 8.1, 1.4 Hz, 2H), 7.64−7.56 (m, 4H), 7.48−7.48 (m, 2H); 13C
NMR (101 MHz, CDCl3) δ 179.9, 137.2, 132.2, 129.8, 129.2, 126.3,
125.9; mp 81−83 °C (lit.31n mp 80−81 °C).
Acetophenone (2r).8 Following general procedure A, colorless
1
liquid (90%, 27 mg): H NMR (600 MHz, CDCl3) δ 7.90 (d, J = 8.4
ASSOCIATED CONTENT
■
Hz, 2H), 7.50 (t, J = 7.4 Hz, 1H), 7.40 (t, J = 7.8 Hz, 2H), 2.54 (s,
3H); 13C NMR (151 MHz, CDCl3) δ 197.8, 136.9, 132.9, 128.4,
128.1, 26.4.
S
* Supporting Information
1H, 13C, and 19F NMR spectra for the products. This material is
1-Phenylpentan-1-one (2s).8 Following general procedure A,
1
colorless liquid (64%, 26 mg): H NMR (600 MHz, CDCl3) δ 7.98−
AUTHOR INFORMATION
7.91 (m, 2H), 7.56−7.51 (m, 1H), 7.44 (dd, J = 10.6, 5.0 Hz, 2H),
3.00−2.94 (m, 2H), 1.72−1.68 (m, 2H), 1.45−1.35 (m, 2H), 0.94 (t, J
= 7.4 Hz, 3H); 13C NMR (151 MHz, CDCl3) δ 200.5, 137.1, 132.8,
128.49, 128.0, 38.3, 26.5, 22.5, 13.9.
■
Corresponding Authors
3-Methyl-1,3-diphenylbutan-1-one (2t).23 Following general
1
Notes
procedure A, colorless liquid (72%, 43 mg): H NMR (400 MHz,
The authors declare no competing financial interest.
CDCl3) δ 7.84−7.79 (m, 2H), 7.51−7.47(m, 1H), 7.39−7.37 (m, 4H),
7.31−7.26 (m, 2H), 7.18−7.13 (m, 1H), 3.31 (s, 2H), 1.50 (s, 6H);
13C NMR (151 MHz, CDCl3) δ 199.0, 148.8, 138.1, 132.6, 128.4,
128.1, 128.0, 125.8, 125.4, 50.9, 37.5, 29.1.
ACKNOWLEDGMENTS
■
We gratefully acknowledge financial support from the National
Natural Science Foundation of China (No. 21272050) and the
Program for New Century Excellent Talents in University of
the Chinese Ministry of Education (NCET-11-0627).
4-Bromobenzaldehyde (4a).24 Following general procedure A,
colorless liquid (72%, 33 mg): 1H NMR (400 MHz, CDCl3) δ 9.98 (s,
1H), 7.78−7.74 (m, 2H), 7.70−7.66 (m, 2H); 13C NMR (151 MHz,
CDCl3) δ 191.0, 135.1, 132.4, 130.9, 129.7.
4-Chlorobenzaldehyde (4b).24 Following general procedure A,
colorless liquid (69%, 24 mg): 1H NMR (400 MHz, CDCl3) δ 9.99 (s,
1H), 7.83 (d, J = 8.4 Hz, 2H), 7.52 (d, J = 8.4 Hz, 2H); 13C NMR
(101 MHz, CDCl3) δ 190.9, 140.9, 134.7, 130.9, 129.5.
REFERENCES
■
(1) Sato, K.; Aoki, M.; Noyori, R. Science 1998, 281, 1646.
(2) Schiaffo, C. E.; Dussault, P. H. J. Org. Chem. 2008, 73, 4688.
(3) (a) Baucherel, X.; Uziel, J.; Juge, S. J. Org. Chem. 2001, 66, 4504.
(b) Wang, A.; Jiang, H. J. Org. Chem. 2010, 75, 2321.
4-Methylbenzaldehyde (4c).24 Following general procedure A,
1
colorless liquid (51%, 15.3 mg): H NMR (600 MHz,CDCl3) δ 9.94
(4) (a) Miyamoto, K.; Tada, N.; Ochiai, M. J. Am. Chem. Soc. 2007,
129, 2772. (b) Miyamoto, K.; Sei, Y.; Yamaguchi, K.; Ochiai, M. J. Am.
Chem. Soc. 2009, 131, 1382.
(s, 1H), 7.75 (d, J = 8.0 Hz, 2H), 7.30 (d, J = 7.9 Hz, 2H), 2.41 (s,
3H); 13C NMR (151 MHz, CDCl3) δ 191.9, 145.5, 134.2, 129.8,
129.7, 21.8.
4-tert-Butylbenzaldehyde (4d).25 Following general procedure
(5) Clennan, E. L.; Pan, G.-L. Org. Lett. 2003, 5, 4979.
1
(6) Zhang, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 28.
(7) (a) Chen, K.; Zhang, P.; Wang, Y.; Li, H. Green Chem. 2014, 16,
2344. (b) Liu, H.; Jiang, X. Synlett 2013, 24, 1311. (c) Liu, H.; Dong,
C.; Zhang, Z.; Wu, P.; Jiang, X. Angew. Chem., Int. Ed. 2012, 51, 12570.
(d) Kim, S. M.; Kim, D. W.; Yang, J. W. Org. Lett. 2014, 16, 2876.
(8) Lin, R. Y.; Chen, F.; Jiao, N. Org. Lett. 2012, 14, 4158.
(9) Wang, T.; Jiao, N. J. Am. Chem. Soc. 2013, 135, 11692.
(10) Hook, J. P. V.; Tobolsky, A. V. J. Am. Chem. Soc. 1958, 80, 779.
(11) Xie, J.; Jiang, H.; Cheng, Y.; Zhu, C. Chem. Commun. 2012, 979.
A, colorless liquid (69%, 28 mg): H NMR (600 MHz, CDCl3) δ
10.07 (s, 1H), 7.91 (d, J = 8.2 Hz, 2H), 7.64 (d, J = 8.2 Hz, 2H), 1.44
(s, 9H); 13C NMR (151 MHz, CDCl3) δ 192.0, 158.4, 134.1, 129.7,
126.0, 35.3, 31.1.
4-Formylphenyl Acetate (4e).26 Following general procedure A,
1
colorless liquid (63%, 26 mg): H NMR (400 MHz, CDCl3) δ 10.00
(s, 1H), 7.94−7.91 (m, 2H), 7.30−7.27 (m, 3H), 2.34 (s, 3H); 13C
NMR (151 MHz, CDCl3) δ 190.9, 168.7, 155.3, 134. 0, 131.2, 122.4,
21.2.
7224
dx.doi.org/10.1021/jo501203a | J. Org. Chem. 2014, 79, 7220−7225