662
J. Lu, P. H. Toy
LETTER
(7) For our work regarding cross-linked polymers, see:
(a) Kwok, M.; Choi, W.; He, H. S.; Toy, P. H. J. Org. Chem.
2003, 68, 9831. (b) Zhao, L. J.; He, H. S.; Shi, M.; Toy,
P. H. J. Comb. Chem. 2004, 6, 680. (c) Zhao, L.-J.; Kwong,
C. K.-W.; Shi, M.; Toy, P. H. Tetrahedron 2005, 61, 12026.
(8) For our work regarding noncross-linked polymers, see:
(a) Harned, A. M.; He, H. S.; Toy, P. H.; Flynn, D. L.;
Hanson, P. R. J. Am. Chem. Soc. 2005, 127, 52. (b) He,
H. S.; Yan, J. J.; Shen, R.; Zhuo, S.; Toy, P. H. Synlett 2006,
563. (c) Kwong, C. K.-W.; Fu, M. Y.; Law, H. C.-H.; Toy,
P. H. Synlett 2010, 2617.
polyaniline salts, and immobilized ionic liquids, to catalyze
the addition of carbon dioxide to epoxides, see: (a) Du, Y.;
Cai, F.; Kong, D.-L.; He, L.-N. Green Chem. 2005, 7, 518.
(b) He, J.; Wu, T.; Zhang, Z.; Ding, K.; Han, B.; Xie, Y.;
Jiang, T.; Liu, Z. Chem. Eur. J. 2007, 13, 6992. (c) Xie, Y.;
Zhang, Z.; Jiang, T.; He, J.; Han, B.; Wu, T.; Ding, K.
Angew. Chem. Int. Ed. 2007, 46, 7255.
(16) (a) Toy, P. H.; Janda, K. D. Tetrahedron Lett. 1999, 40,
6329. (b) Toy, P. H.; Reger, T. S.; Janda, K. D. Aldrichimica
Acta 2000, 33, 87. (c) Toy, P. H.; Reger, T. S.; Garibay, P.;
Garno, J. C.; Malikayil, J. A.; Liu, G.-Y.; Janda, K. D.
J. Comb. Chem. 2001, 3, 117. (d) Choi, M. K. W.; Toy, P.
H. Tetrahedron 2004, 60, 2903.
(9) Chung, C. W. Y.; Toy, P. H. J. Comb. Chem. 2007, 9, 155.
(10) Kwong, C. K.-W.; Huang, R.; Zhang, M.; Shi, M.; Toy, P.
H. Chem. Eur. J. 2007, 13, 2369.
(17) See Supporting Information for details.
(11) For selected reviews regarding the addition of carbon
dioxide to epoxides to form cyclic carbonates, see: (a) Dai,
W.-L.; Luo, S.-L.; Yin, S.-F.; Au, C.-T. Appl. Catal., A 2009,
366, 2. (b) Sakakura, T.; Kohno, K. Chem. Commun. 2009,
1312. (c) North, M.; Pasquale, R.; Young, C. Green Chem.
2010, 12, 1514.
(12) For the organocatalytic addition of carbon dioxide to
epoxides, see: (a) Shiels, R. A.; Jones, C. W. J. Mol. Catal.
A: Chem. 2007, 261, 160; and references cited therein.
(b) Qi, C.; Jiang, H.; Wang, Z.; Zou, B.; Yang, S. Synlett
2007, 255. (c) Barkakaty, B.; Morino, K.; Sudo, A.; Endo, T.
Green Chem. 2010, 12, 42.
(13) For selected reviews regarding polymer-supported
organocatalysts, see: (a) Benaglia, M.; Puglisi, A.; Cozzi, F.
Chem. Rev. 2003, 103, 3401. (b) Benaglia, M. New J. Chem.
2006, 30, 1525. (c) Cozzi, F. Adv. Synth. Catal. 2006, 348,
1367. (d) Gruttadauria, M.; Giacalone, F.; Noto, R. Chem.
Soc. Rev. 2008, 37, 1666. (e) Kristensen, T. E.; Hansen, T.
Eur. J. Org. Chem. 2010, 3179.
(14) For the use of polymer-supported organocatalysts in the
addition of carbon dioxide to epoxides, see: (a) Xie, H.;
Duan, H.; Li, S.; Zhang, S. New J. Chem. 2005, 29, 1199.
(b) Du, Y.; Wang, J.-Q.; Chen, J.-Y.; Cai, F.; Tian, J.-S.;
Kong, D.-L.; He, L.-N. Tetrahedron Lett. 2006, 47, 1271.
(c) Jagtap, S. R.; Raje, V. P.; Samant, S. D.; Bhanage, B. M.
J. Mol. Catal. A: Chem. 2007, 266, 69. (d) Qi, C.-R.; Jiang,
H.-F.; Wang, Z.-Y.; Zou, B. Chin. J. Chem. 2007, 25, 1051.
(e) Qi, C.; Ye, J.; Zeng, W.; Jiang, H. Adv. Synth. Catal.
2010, 352, 1925.
(18) General Procedure for CO2 Addition Reactions
Epoxide 7a–j (22.4 mmol), CH2Cl2 (0.5 mmol), and 4 (0.224
mmol) were placed in a 25 mL stainless-steel autoclave.
Carbon dioxide was then introduced into the reactor at an
initial pressure of 20 bar at r.t. The reactor was then heated
to 120 °C, and the pressure was adjusted to 30 bar. The
reaction mixture was stirred under these conditions for the
indicated time, and then the autoclave was cooled using an
ice bath. After releasing the pressure, compound 4 was
filtered off and washed with CH2Cl2. The filtrate was
concentrated in vacuo to afford the product 8a–j. The
identity of the products was confirmed by 1H NMR.
(19) Yue, Y.; Yu, X.-Q.; Pu, L. Chem. Eur. J. 2009, 15, 5104.
(20) (a) Bollini, M.; González, M.; Bruno, A. M. Tetrahedron
Lett. 2009, 50, 1507. (b) Ko, K.; Nakano, K.; Watanabe, S.;
Ichikawa, Y.; Kotsuki, H. Tetrahedron Lett. 2009, 50, 4025.
(c) Deb, I.; Shanbhag, P.; Mobin, S. M.; Namboothiri, I. N.
N. Eur. J. Org. Chem. 2009, 4091. (d) Mhasni, O.; Rezgui,
F. Tetrahedron Lett. 2010, 51, 586. (e) Naidu, K. C.; Babu,
G. R.; Gangaiah, L.; Mukkanti, K.; Madhusudhan, G.
Tetrahedron Lett. 2010, 51, 1226. (f) Angelini, T.;
Fringuelli, F.; Lanari, D.; Pizzo, F.; Vaccaro, L. Tetrahedron
Lett. 2010, 51, 1566. (g) Goncalves, S.; Nicolas, M.;
Wagner, A.; Baati, R. Tetrahedron Lett. 2010, 51, 2348.
(h) Aoki, S.; Kotani, S.; Sugiura, M.; Nakajima, M.
Tetrahedron Lett. 2010, 51, 3547. (i) Hudhomme, P. Synlett
2010, 1331. (j) Vuluga, D.; Legros, J.; Crousse, B.; Bonnet-
Delpon, D. Chem. Eur. J. 2010, 16, 1776. (k) Helou, M.;
Miserque, O.; Brusson, J.-M.; Carpentier, J.-F.; Guillaume,
S. M. Chem. Eur. J. 2010, 16, 13805.
(15) For the use of other polymers, such as ion-exchange resins,
Synlett 2011, No. 5, 659–662 © Thieme Stuttgart · New York