ACCEPTED MANUSCRIPT
6
Tetrahedron
1
3
Hz, 1H), 7.59 (t, J = 7.3 Hz, 1H), 7.48 (d, J = 7.7 Hz, 1H), 7.37
Hz, 2H). C NMR (75 MHz, CDCl
3
) δ 193.28, 136.48, 134.99,
1
3
(
t, J = 7.4 Hz, 1H), 3.25 -3.01 (m, 1H), 2.88-2.48 (m, 1H). C
133.38, 131.00, 130.16, 128.77, 128.22, 126.66, 124.58.
36
o
NMR (75 MHz, CDCl
3
) δ 206.96, 155.03, 136.88, 134.45,
1-Pyrenecarboxaldehyde (4h) Yellow solid; mp 122-123 C (lit.
o
1
1
3
27.10, 126.56, 123.50, 36.04, 25.63.
,4-Dihydronaphthalen-1(2H)-one (2o) Colourless liquid; H
) δ 8.13-7.92 (m, 1H), 7.47 (m, 1H),
.42-7.16 (m, 2H), 2.97 (t, J = 5.5 Hz, 2H), 2.66 (m, 2H), 2.25-
120-123 C); H NMR (300 MHz, CDCl ) δ 10.72 (s, 1H), 9.33
3
24
1
(d, J = 9.3 Hz, 1H), 8.36 (d, J = 7.9 Hz, 1H), 8.23 (dd, J = 5.9,
3.6 Hz, 3H), 8.16 (d, J = 8.6 Hz, 2H), 8.04 (dd, J = 13.9, 8.2 Hz,
NMR (300 MHz, CDCl
3
1
3
7
2
1
2
3
2H). C NMR (75 MHz, CDCl ) δ 192.64, 134.82, 130.66,
1
3
.02 (m, 2H) C NMR (75 MHz, CDCl
3
) δ 198.13, 144.28,
130.36, 130.14, 129.82, 126.68, 126.44, 126.14, 123.97, 123.79,
123.33, 122.33.
33.17, 132.35, 128.57, 126.87, 126.37, 38.94, 29.46, 23.07.
-Aminoacetophenone (2p) Colourless liquid; H NMR (500
) δ 7.73 (d, J = 8.0 Hz, 1H), 7.28 (m, 1H), 6.67 (m,
1
9
1
34
1
MHz, CDCl
3
Phenylacrolein (4i) Colourless liquid; H NMR (300 MHz,
CDCl ) δ 9.71 (d, J = 7.7 Hz, 1H), 7.58 (dd, J = 6.5, 2.9 Hz, 2H),
7.51 (s, 1H), 7.49-7.37 (m, 4H), 6.73 (dd, J = 15.9, 7.7 Hz, 1H).
13
2
2
3
H), 6.30 (br, 2H), 2.59 (s, 3H). C NMR (126 MHz, CDCl
00.76, 150.36, 134.39, 132.05, 118.19, 117.24, 115.68, 27.83.
-Methylcyclohex-2-enone (2q) Colourless liquid; H NMR
3
) δ
3
25
1
13
C NMR (75 MHz, CDCl
3
) δ 191.45, 150.55, 131.77, 129.05,
(
6
500 MHz, CDCl ) δ 5.89 (s, 1H), 2.39-2.32 (m, 2H), 2.29 (t, J =
126.88, 126.29.
3
1
3
4c
1
.0 Hz, 2H), 2.05-1.98 (m, 2H), 1.97 (s, 3H). C NMR (126
) δ 199.56, 162.76, 126.51, 36.91, 30.84, 24.35,
2-Furfural (4j) Colourless liquid; H NMR (300 MHz, CDCl
9.68 (s, 1H), 7.70 (s, 1H), 7.26 (s, 1H), 6.77-6.35 (m, 1H). C
3
) δ
13
MHz, CDCl
3
2
2
2.47.
3
-Acetylfuran (2r) Yellow liquid; H NMR (300 MHz, CDCl )
NMR (75 MHz, CDCl
112.55.
2-Thenaldehyde (4k) Colourless liquid; H NMR (300 MHz,
CDCl ) δ 9.96 (s, 1H), 8.21-7.58 (m, 2H), 7.52-7.06 (m, 1H). C
3
NMR (75 MHz, CDCl
127.78.
3
) δ 177.78, 152.79, 148.08, 121.29,
2
6
1
4
c
1
δ 7.59 (s, 1H), 7.19 (d, J = 3.5 Hz, 1H), 6.55 (m, 1H), 2.49 (s,
1
3
13
3
1
2
H). C NMR (126 MHz, CDCl
3
) δ 186.66, 152.75, 146.41,
17.24, 112.20, 25.91.
-Acetylthiophene (2s) Colourless liquid; H NMR (300 MHz,
3
) δ 182.47, 143.34, 135.90, 134.57,
27
1
3
7
1
CDCl ) δ 7.71 (d, J = 3.7 Hz, 1H), 7.65 (d, J = 4.9 Hz, 1H), 7.19-
3-Pyridinecarboxaldehyde (4l) Colourless liquid; H NMR (500
MHz, CDCl ) δ 10.14 (s, 1H), 9.10 (d, J = 1.3 Hz, 1H), 8.86 (dd,
J = 4.7, 1.2 Hz, 1H), 8.19 (dd, J = 7.8, 1.7 Hz, 1H), 7.50 (dd, J =
3
13
7
1
3
.07 (m, 1H), 2.58 (s, 3H). C NMR (126 MHz, CDCl
3
) δ
3
90.70, 144.52, 133.79, 132.54, 128.15, 26.86.
28
1
13
-Acetylpyridine (2t) Colourless liquid; H NMR (500 MHz,
) δ 9.18 (d, J=1.3 Hz, 1H), 8.90-8.68 (m, 1H), 8.25 (d, J =
7.8, 4.9 Hz, 1H). C NMR (126 MHz, CDCl
3
) δ 190.75, 154.62,
CDCl
.0 Hz, 1H), 7.44 (dd, J = 7.9, 4.8 Hz, 1H), 2.66 (s, 3H).
3
151.89, 135.72, 131.32, 123.99.
3-Phenylpropanal (4m) Slightly Yellow liquid; H NMR (500
13
4c
1
8
C
NMR (126 MHz, CDCl
3
) δ 196.63, 153.40, 149.80, 135.35,
MHz, CDCl
8.7 Hz, 3H), 2.99 (t, J = 7.6 Hz, 2H), 2.81 (m, 2H). C NMR
(126 MHz, CDCl ) δ 201.61, 140.34, 128.62, 128.48, 128.30,
126.32, 45.28, 28.13.
3
) δ 9.85 (s, 1H), 7.32 (t, J = 7.5 Hz, 2H), 7.23 (t, J =
13
1
2
32.15, 123.53, 26.60.
-Acetylpyridine (2u) Colourless liquid; H NMR (500 MHz,
29
1
3
CDCl
m, 1H), 7.49 (m, 1H), 2.75 (s, 3H). C NMR (126 MHz, CDCl
δ 199.85, 153.45, 148.87, 136.70, 126.97, 121.45, 25.61.
3
) δ 8.71 (d, J = 4.5 Hz, 1H), 8.06 (d, J = 7.8 Hz, 1H), 7.85
13
4c
1
(
3
)
Octanal (5n) Slightly yellow liquid; H NMR (300 MHz,
CDCl ) δ 9.76 (s, 1H), 2.41 (t, J = 7.5 Hz, 2H), 1.61 (m, 2H),
3
4
c
1
13
Benzaldehyde (4a) Colourless liquid; H NMR (300 MHz,
1.43-1.13 (m, 8H), 0.88 (t, J = 6.8 Hz, 3H). C NMR (75 MHz,
CDCl ) δ 10.03 (s, 1H), 7.88 (m, 2H), 7.64 (m, 1H), 7.54 (m,
CDCl ) δ 202.71, 43.72, 31.43, 28.94, 28.83, 22.39, 21.89,
13.84..
3
3
1
3
2
1
3
4
H). C NMR (75 MHz, CDCl
28.96.
3
) δ 192.30, 134.40, 129.68,
30
o
,4-Dimethoxybenzaldehyde (4b) White solid; mp 45-47 C (lit.
Acknowledgments
o
1
2-45 C); H NMR (500 MHz, CDCl
3
) δ 9.88 (s, 1H), 7.48 (dd, J
=
8.2 Hz, 1.9 Hz, 1H), 7.43 (d, J = 1.8 Hz, 1H), 7.00 (d, J = 8.2
Financial supports by the the Priority Academic Program
Development of Jiangsu Higher Education Institutions (PAPD)
and the National Nature Science Foundation of China (NSFC)
(grant number 30870625) are gratefully acknowledged.
1
3
Hz, 1H), 3.99 (s, 3H), 3.97 (s, 3H). C NMR (126 MHz, CDCl
δ 190.83, 154.45, 149.58, 130.10, 126.80, 110.38, 108.91, 56.14,
3
)
5
4
5.95.
-Dimethylaminobenzaldehyde (4c) White solid; mp 72-73 C
31
o
o
1
(
lit. 71-71.5 C); H NMR (300 MHz, CDCl
3
) δ 9.74 (d, J = 2.5
References and notes
Hz, 1H), 7.74 (dd, J = 9.2, 2.3 Hz, 2H), 6.71 (dd, J = 9.2, 2.1 Hz,
1
3
2
1
H), 3.21-2.95 (m, 7H). C NMR (75 MHz, CDCl
54.05, 131.67, 124.75, 118.75, 110.71, 39.78.
3
) δ 189.98,
1
2
.
.
(a) Lee, D. G.; Stewart, R. J. Am. Chem. Soc. 1964, 86, 3051-3056;
(b) Collins, J. C.; Hess, W. W.; F. J. Frank. Tetrahedron Lett.
1968, 9, 3363-3366; (c) Turner, D. L. J. Am. Chem. Soc. 1954, 76,
5175-5176; (d) Highet, R. J.; Wildman, W. C. J. Am. Chem. Soc.
1955, 77, 4399-4401.
32
o
4
-Formylbenzonitrile (4d) White solid; mp 83-85 C (lit. 80-81
o
1
C); H NMR (300 MHz, CDCl
3
) δ 10.10 (s, 1H), 8.02 (dd, J =
13
7
.3, 1.2 Hz, 2H), 7.87 (d, J = 8.1 Hz, 2H). C NMR (75 MHz,
Brackman, W.; Gaasbeek, C. J.; Smit, P. J. Recl. Trav. Chim.
Pays-Bas. 1966, 85, 437-445.
CDCl ) δ 190.47, 138.50, 132.68, 129.66, 117.50, 117.32.
3
3
3
1
3
-Fluorobenzaldehyde (4e) Colourless liquid; H NMR (300
MHz, CDCl ) δ 9.99 (s, 1H), 8.33- 7.70 (m, 2H), 7.52-6.89 (m,
H). C NMR (75 MHz, CDCl ) δ 189.76, 167.43, 164.03,
32.24, 131.53, 131.40, 115.71, 115.41.
3. Semmelhack,M. F.; Schmid, C. R.;Cortés,D. A.;Chou, C. S. J.
Am. Chem. Soc. 1984, 106, 3374-3376.
3
1
3
4
.
(a) Gamez, P.; Arends, I. W. C. E.; Reedijk, J.; Sheldon, R. A.
Chem. Commun. 2003, 2414-2415; (b) Kumpulainen, E. T. T.;
Koskinen, A. M. P. Chem. - Eur. J. 2009, 15, 10901-10911; (c)
Hoover, J. M.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 16901-
16910.
2
1
3
34
o
4
-bromobenzaldehyde (4f) White solid; mp 56-57 C (lit. 57
o
1
3
C); H NMR (300 MHz, CDCl ) δ 9.95 (s, 1H), 7.71 (dd, J =
1
3
1
1
3.2, 6.6 Hz, 4H). C NMR (75 MHz, CDCl ) δ 190.54, 134.50,
31.88, 130.43, 129.21.
5. (a) Steves, J. E.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 15742-
5745. (b) Sasano, Y.; Nagasawa, S.; Yamazaki, M.; Shibuya, M.;
3
1
3
5
o
o
Park, J.; Iwabuchi, Y. Angew. Chem. Int. Ed. 2014, 53, 3236-3240.
6. Zhang, G.; Han, X.; Luan, Y.; Wang, Y.; Wen, Xin.; Ding, C.
Chem. Commun. 2013, 49, 7908-7910.
2
-Naphthaldehyde (4g) White solid; mp 58-59 C (lit. 58 C);
1
H NMR (300 MHz, CDCl
3
) δ 10.38 (s, 1H), 9.25 (d, J = 8.5 Hz,
1
H), 8.07 (d, J = 8.2 Hz, 1H), 7.96 (d, J = 7.0 Hz, 1H), 7.90 (d, J
7
.
(a) Herr, R. J. Bioorg. Med. Chem. 2002, 10, 3379-3393; (b)
Myznikov, L.V.; Hrabalek, A.; Koldobskii, G. I. Chem.
Heterocycl. Compd. 2007, 43, 1-9.
=
8.1 Hz, 1H), 7.67 (dd, J = 13.8, 6.1 Hz, 1H), 7.59 (q, J = 7.3