LETTER
Rasta Resin-TBD as a Reusable Catalyst for Transesterification Reactions
1873
Table 2 Reactions of Various Alcohols with Vinyl Acetatea
Acknowledgement
1
(10 mol%)
This research was supported financially by the University of Hong
Kong and the Research Grants Council of the Hong Kong S. A. R.,
P. R. of China (Project No. HKU 705209P).
O
O
THF, 60 °C, 24 h
ROH
+
O
RO
26
24
25
Entry
Substrate
Product
Isolated yield
Supporting Information for this article is available online at
(
%)
http://www.thieme-connect.com/ejournals/toc/synlett. SnuIpofoipmngr irtSatnoIuipfog
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References and Notes
OH
9
8
O
O
b
1
(97)
(1) (a) Patterson, T.; Dinsdale, R.; Esteves, S. Energy Fuels
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(
60)c
24a
2
6a
OH
O
2
3
97
91
(2) (a) Leung, D. Y. C.; Wu, X.; Leung, M. K. H. Appl. Energy
2
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2
4b
4c
26b
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O
O
OH
OH
O
O
2
2
6c
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(
(
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1
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4d
4e
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O
5
6
OH
O
55
17
8
93.
2
(6) For selected reviews and a book chapter regarding TBD as a
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2
006, 737. (b) Coles, M. P. Chem. Commun. 2009, 3659.
O
(
c) Ishikawa, T. In Superbases for Organic Synthesis:
Guanidines, Amidines, Phosphazenes and Related
OH
O
Organocatalysts; Ishikawa, T., Ed.; John Wiley & Sons,
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24f
26f
4
3, 2093. (e) Taylor, J. E.; Bull, S. D.; Williams, J. M. J.
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OH
O
7
0
0
(
O
2
4g
4h
26g
7
7, 241. (c) Fringuelli, F.; Pizzo, F.; Vittoriani, C.; Vaccaro,
O
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OH
O
8
2
2
6h
a
Reaction conditions: alcohol 24 (1.0 mmol), 25 (1.2 mmol), 1 (0.10
mmol), and THF (1.0 mL) heated at 60 ºC for 24 h.
b
Result using recovered 1.
Fujikawa, S. Tetrahedron Lett. 2012, 53, 1075.
c
Result using 19 (0.10 mmol) as the catalyst.
(8) Bonollo, S.; Lanari, D.; Angelini, T.; Pizzo, F.; Marrocchi,
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(
9) See Supporting Information for details.
sitioning of the TBD groups of 1 on flexible grafts that are
more accessible to dissolved substrate molecules than the
TBD groups of 19, which are located in the interior of the
heterogeneous polymer.
(
10) Venkat Reddy, C. R.; Fetterly, B. M.; Verkade, J. G. Energy
Fuels 2007, 21, 2466.
(11) General Procedure for the Transesterification of 17:
Sunflower oil 17 (0.500 g, 0.59 mmol), MeOH (2.0 mL), and
1
(0.095 g, 0.24 mmol) were added to a 7-mL vial equipped
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Georg Thieme Verlag Stuttgart · New York
Synlett 2013, 24, 1870–1874