RSC Advances
DOI: 10.1039/C5RA07681A
O
O
OH
0
.5 mmol KOH,
and Y. M. A. Yamada, Org. Lett., 2011, 13, 3892ꢀ3895; (f) O. Saidi,
A. J. Blacker, M. M. Farah, S. P. Marsden and J. M. Williams,
Angew. Chem. Int. Ed., 2009, 48, 7375ꢀ7378.
OH
OH
OH
2 mL Toluene, Ar
(
a)
+
+
+
50 oC, 4 h
1
cat-2
.25 mmol
cat-2
O
cat-2-OH
OH
0
1 mmol
cat-2 : cat-2-OH = 8 : 92
O
45 4. (a) M. Ousmane, G. Perrussel, Z. Yan, J. M. Clacens, F. De Campo
and M. PeraꢀTitus, J. Catal., 2014, 309, 439ꢀ452; (b) Y. Zhang, X.
Qi, X. Cui, F. Shi and Y. Deng, Tetrahedron Lett., 2011, 52, 1334ꢀ
0
.5 mmol KOH,
2 mL Toluene, Ar
+
(
b)
150 oC, 4 h
O
O
O
O
O
O
cat-3
.25 mmol
cat-3
O
cat-3-OH
0
1 mmol
cat-3 : cat-3-OH = 28 : 72
1
338; (c) R. Ghosh and A. Sarkar, J. Org. Chem., 2011, 76, 8508ꢀ
O
OH
8512.
0
.5 mmol KOH,
2 mL Toluene, Ar
(
c)
d)
+
50 5. S. L. Feng, C. Z. Liu, Q. Li, X. C. Yu and Q. Xu, Chin. Chem. Lett.,
1
50 oC, 4 h
O
O
O
2
011, 22, 1021ꢀ1024.
cat-9
.25 mmol
1 mmol
cat-9
cat-9-OH
0
cat-9 : cat-9-OH = 98 : 2
6. (a) W. He, L. Wang, C. Sun, K. Wu, S. He, J. Chen, P. Wu and Z.
Yu, Chem. Eur. J., 2011, 17, 13308ꢀ13317; (b) L. Wang, W. He, K.
Wu, S. He, C. Sun and Z. Yu, Tetrahedron Lett., 2011, 52, 7103ꢀ
7107.
OH
O
OH
NH2 0.5 mmol KOH,
2 mL Toluene, Ar
O
(
+
+
1
50 oC, 4 h
cat-2-OH
.25 mmol
1 mmol/1 mmol
cat-2
O
cat-2-OH
cat-2 : cat-2-OH = 41 : 59
55
60
0
7
.
(a) Y. S. Demidova, I. L. Simakova, J. Wärnå, A. Simakov and D. Y.
Murzin, Chem. Eng. J., 2014, 238, 164ꢀ171; (b) Y. Wang, D. Zhu, L.
Tang, S. Wang and Z. Wang, Angew. Chem. Int. Ed., 2011, 50, 8917ꢀ
8921; (c) L. He, X. B. Lou, J. Ni, Y. M. Liu, Y. Cao, H. Y. He and K.
N. Fan, Chem. Eur. J., 2010, 16, 13965ꢀ13969.
OH
OH
NH2 0.5 mmol KOH,
2 mL Toluene, Ar
O
(e)
+
O
+
O
150 oC, 4 h
O
O
O
O
cat-3-OH
.25 mmol
1 mmol/1 mmol
cat-3
O
cat-3-OH
0
cat-3 : cat-3-OH = <<1 : 99
OH
OH
NH2 0.5 mmol KOH,
2 mL Toluene, Ar
O
8. A. Abdukader, H. Jin, Y. Cheng and C. Zhu, Tetrahedron Lett., 2014,
5, 4172ꢀ4174.
(
f)
+
+
O
150 oC, 4 h
O
O
5
cat-9-OH
.25 mmol
1 mmol/1 mmol
cat-9
cat-9-OH
cat-9 : cat-9-OH = >>100 : 1
0
9. (a) I. Geukens, F. Vermoortele, M. Meledina, S. Turner, G. Van
Tendeloo and D. E. De Vos, Appl. Catal., A: Chem., 2014, 469, 373ꢀ
379; (b) X. Cui, Y. Zhang, F. Shi and Y. Deng, Chem. Eur. J., 2011,
6
7
5
0
1
7, 1021ꢀ1028; (c) K.ꢀI. Shimizu, K. Shimura, M. Nishimura and A.
Satsuma, RSC Adv., 2011, 1, 1310ꢀ1317.
1
0. (a) K.ꢀi. Shimizu, K. Kon, W. Onodera, H. Yamazaki and J. N.
Kondo, ACS Catal., 2013, 3, 112ꢀ117; (b) K.ꢀi. Shimizu, N. Imaiida,
K. Kon, S. M. A. Hakim Siddiki and A. Satsuma, ACS Catal., 2013,
Scheme 2. Reaction mechanism exploration. The results were determined
by GCꢀMS with external standard method.
3
, 998ꢀ1005.
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5
In conclusion, an efficient molecularꢀdefined organocatalyst
was developed for the transferꢀhydrogenation reactions including
alcohol amination and carbonyl compound reduction. The ketone
and alcohol groups inside the catalyst are the active sites of the
catalyst. To the best of our knowledge, this is the first time to
show that ketone with a specific structure can be an active
catalyst for transferꢀhydrogenation reactions. It should be helpful
for us to understand the transferꢀhydrogenation reaction and also
provides an efficient methodology for such transformations.
1
2
7
8
8
5
0
5
Eur. J., 2013, 19, 3665ꢀ3675; (c) A. MartínezꢀAsencio, D. J. Ramón
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10
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5
Tetrahedron Lett., 2010, 51, 2048ꢀ2051; (c) R. Martinez, D. J.
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1
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Notes and references
15
20
25
30
35
40
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Centre
for Green Chemistry and Catalysis, Lanzhou Institute of Chemical
Physics, Chinese Academy of Sciences, Lanzhou, 730000, China. Fax:
86-931-8277088; Tel: +86-931-4968142; E-mail: fshi@licp.cas.cn
Electronic Supplementary Information (ESI) available: The details about
the characterization of isolated compounds. See DOI: 10.1039/b000000x/
+
†
90
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4
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