Recent Progress in Carbonylation of Epoxides

doi:10.3724/SP.J.1088.2012.20515

Abstract

Abstract: Carbonylation reactions that introduce carbonyl moiety into organic and inorganic substrates have the advantages of atom economical selectivity and environmental benignancy. Recently, it has been one of the challenging and attractive subjects in the field of value-added utilization of C₁resources and a bridge between petrochemical industry and C₁ chemistry. The important transformation has drawn considerable attention from both academia and industry. We aim to present recent progress in cobalt carbonyl complexes catalyzed carbonylation of epoxides, including ring-expansion carbonylation, ring-opening carbonylative copolymerization, and ring-opening carbonylation. The development prospects are also discussed.

Key words: epoxide, ring-expansion carbonylation, ring-opening carbonylative copolymerization, ring-opening carbonylation, reaction mechanism

FAN Qi-Jia, LIU Jian-Hua, CHEN Jing, XIA Chun-Gu. Recent Progress in Carbonylation of Epoxides[J]. Chinese Journal of Catalysis, 2012, 33(9): 1435-1447.

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References

1 Sneeden R P A, Tkatchenko I, Villeurbanne C N R S. In: Wilkinson G, Stone F G A, Abel E W ed. Comprehensive Organometallic Chemistry. Vol. 8. New York: Pergamon Press, 1982. 1
2 Roelen O. DE 849 548. 1938
3 Kollár L. Modern Carbonylation Methods. Weinheim: John Wiley & Sons Inc, 2008. 1
4 刘建华, 陈静, 孙伟, 夏春谷. 催化学报 (Liu J H, Chen J, Sun W, Xia Ch G. Chin J Catal), 2010, 31: 1
5 刘建华, 陈静, 夏春谷. 石油化工 (Liu J H, Chen J, Xia Ch G. Petrochem Technol), 2010, 11: 1189
6 Lu X B, Darensbourg D J. Chem Soc Rev, 2012, 41: 1462
7 Klaus S, Lehenmeier M W, Anderson C E, Rieger B. Coord Chem Rev, 2011, 255: 1460
8 North M, Pasquale R, Young C. Green Chem, 2010: 1514
9 Darensbourg D J, Holtcamp M W. Coord Chem Rev, 1996, 153: 155
10 高志文, 肖林飞, 陈静, 夏春谷. 催化学报 (Gao Zh W, Xiao L F, Chen J, Xia Ch G. Chin J Catal), 2008, 29: 831
11 Church T L, Getzler Y D Y L, Byrne C M, Coates G W. Chem Commun, 2007: 657
12 Khumtaveeporn K, Alper H. Acc Chem Res, 1995, 28: 414
13 Böttcher T, Sieber S A. Med Chem Commun, 2012, 3: 408
14 Wang Y, Tennyson R L, Romo D. Heterocycles, 2004, 64: 605
15 Pommier A, Pons J M. Synthesis, 1993: 441
16 Wu J, Yu T L, Chen C T, Lin C C. Coord Chem Rev, 2006, 250: 602
17 刘建华, 陈静. 化学进展 (Liu J H, Chen J. Progr Chem), 2004, 16: 989
18 Drent E, Kragtwijk E. EP 577 206. 1994
19 Lee J T, Thomas P J, Alper H. J Org Chem, 2001, 66: 5424
20 Molnar F, Luinstra G A, Allmendinger M, Reiger B. Chem Eur J, 2003, 9: 1273
21 Allmendinger M, Eberhardt R, Luinstra G A, Molnar F, Rieger B. Z Anorg Allg Chem, 2003, 629: 1347
22 Getzler Y D Y L, Mahadevan V, Lobkovsky E B, Coates G W. J Am Chem Soc, 2002, 124: 1174
23 Mahadevan V, Getzler Y D Y L, Coates G W. Angew Chem, Int Ed, 2002, 41: 2781
24 Schmidt J A R, Mahadevan V, Getzler Y D Y L, Coates G W. Org Lett, 2004, 6: 373
25 Getzler Y D Y L, Mahadevan V, Lobkovsky E B, Coates G W. Pure Appl Chem, 2004, 76: 557
26 Schmidt J A R, Lobkovsky E B, Coates G W. J Am Chem Soc, 2005, 127: 11426
27 Kramer J W, Lobkovsky E B, Coates G W. Org Lett, 2006, 8: 3709
28 Ganji P, Doyle D J, Ibrahim H. Org Lett, 2011, 13: 3142
29 Chen Q, Mulzer M, Shi P, Beuning P J, Coates G W, O'Doherty G A. Org Lett, 2011, 13: 6592
30 Stirling A, Iannuzzi M, Parrinello M, Molnar F, Bernhart V, Luinstra G A. Organometallics, 2005, 24: 2533
31 Church T L, Getzler Y D Y L, Coates G W. J Am Chem Soc, 2006, 128: 10125
32 Kramer J W, Joh D Y, Coates G W. Org Lett, 2007, 9: 5581
33 Getzler Y D Y L, Kundnani V, Lobkovsky E B, Coates G W. J Am Chem Soc, 2004, 126: 6842
34 Rowely J M, Lobkovsky E B, Coates G W. J Am Chem Soc, 2007, 129: 4948
35 Furukawa J, Iseda H, Saegusa T, Fujii H. Die Makromol Chem, 1965, 89: 263
36 Takeuchi D, Sakaguchi Y, Osakada K. J Polym Sci Part A, 2002, 40: 4530
37 Lee J T, Alper H. Macromolecules, 2004, 37: 2417
38 Allmendinger M, Eberhardt R, Luinstra G A, Rieger B. J Am Chem Soc, 2002, 124: 5646
39 Allmendinger M, Eberhardt R, Luinstra G A, Rieger B. Macromol Chem Phys, 2003, 204: 564
40 Nakano K, Fumitaka K, Nozaki K. J Polym Sci Part A, 2004, 42: 4666
41 Liu G, Jia L. J Am Chem Soc, 2004, 126: 14716
42 Allmendinger M, Zintl M, Eberhardt R, Luinstra G A, Molnar F, Rieger B. J Organomet Chem, 2004, 689: 971
43 Allmendinger M, Molnar F, Zintl M, Luinstra G A, Preishuber-Pflügl P, Rieger B. Chem Eur J, 2005, 11: 5327
44 Brulé E, Guo J, Coates G W, Thomas C M. Macromol Rapid Commun, 2011, 32: 169
45 Reichardt R, Rieger B. Adv Polym Sci, 2012, 245: 49
46 Dunn E W, Coates G W. J Am Chem Soc, 2010, 132: 11412
47 Roos L, Goetz R W, Orchin M. J Org Chem, 1965, 30: 3023
48 Rosenthal A, Kan G. Tetrahdron Lett, 1967, 8: 477
49 Powell J B, Mullin S B, Weider P R, Eubanks D C, Arhan-cet J P. US 5 770 776. 1998
50 Lee B N, Yang D J, Byun Y H. US 6 348 611. 2002
51 Hamada K, Baba K, Hagihara N. Memoirs Inst Sci Ind Res, Osaka Univ, 1957, 14: 207
52 Lenel P O. Proc Chem Soc, 1958, 50
53 Yokokawa C, Watanabe Y, Takegami Y. Bull Chem Soc Jpn, 1964, 37: 677
54 Weber R, Englert U, Ganter B, Keim W, Möthrath M. Chem Commun, 2000: 1419
55 Nakano K, Katayama M, Ishihara S, Hiyama T, Nozaki K. Synlett, 2004: 1367
56 Seki Y, Murai S, Yamamoto I, Sonoda N. Angew Chem, Int Ed, 1977, 16: 789
57 Tsuji Y, Kobayashi M, Okuda F, Watanabe Y. J Chem Soc, Chem Commun, 1989: 1253
58 Watanabe Y, Nishiyama K, Zhang K, Okuda F, Kondo T, Tsuji Y. Bull Chem Soc Jpn, 1994, 67: 879
59 Goodman S N, Jacobsen E N. Angew Chem, Int Ed, 2002, 41: 4703
60 Eisenmann J, Yamartino R, Howard J. J Org Chem, 1961, 26: 2102
61 McClure J D, Fisher R F. US 3 260 738. 1966
62 Kawabata Y, Tanaka M, Hayashi T, Ogata I. Nippon Kagaku Kaishi, 1979, 5: 635
63 Lee B N, Chen B S. US 6 348 632. 2002
64 Hinterding K, Jacobsen E N. J Org Chem, 1999, 64: 2164
65 Balázs A, Benedek C, Szalontai G, Torös S. Steroids, 2004, 69: 271
66 Kim H S, Bae J Y, Lee J S, Jeong II C, Choi D K, Kang S O, Cheong M. Appl Catal A, 2006, 301: 75
67 Liu J H, Chen J, Xia Ch G. J Mol Catal A, 2006, 250: 232
68 Liu J H, Wu H, Xu L W, Chen J, Xia Ch G. J Mol Catal A, 2007, 269: 97
69 Denmark S E, Ahmad M. J Org Chem, 2007, 72: 9630
70 Deng F G, Hu B, Sun W, Chen J, Xia Ch G. Dalton Trans, 2007: 4262
71 Lü Z G, Wang H S, Li J A, Guo Z M. Res Chem Intermed, 2010, 36: 1027
72 Hamasaki A, Muto A, Haraguchi S, Liu X, Sakakibara T, Yokoyama T, Tokunaga M. Tetrahedron Lett, 2011, 52: 6869

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