Substrate-Controlled Product Divergence: Conversion of CO2 into Heterocyclic Products

Angewandte Chemie - International Edition

Volumn 55, Issue 12, 2016, Pages 3972-3976

  Rintjema, Jeroen ^a   Epping, Roel ^a   Fiorani, Giulia ^a   Martín, Eddy ^a   Escudero Adán, Eduardo C ^a   Kleij, Arjan W ^a,b  

^a BARCELONA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Spain)

^b INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

carbon dioxide fixation; heterocycles; homogeneous catalysis; Lewis acids; small ring systems

Indexed keywords

CARBON; CATALYSIS; NUCLEOPHILES; ORGANIC COMPOUNDS; SCAFFOLDS;

CARBON DIOXIDE FIXATION; HETEROCYCLES; HOMOGENEOUS CATALYSIS; LEWIS ACID; SMALL RING SYSTEMS;

CARBON DIOXIDE;

EID: 84975736052     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201511521     Document Type: Article

References (61)

1. Q. Liu, L. Wu, R. Jackstell, M. Beller, Nat. Commun. 2015, 6, 5933;
2. M. Aresta, A. Dibenedetto, A. Angelini, Chem. Rev. 2014, 114, 1709;
3. N. Kielland, C. J. Whiteoak, A. W. Kleij, Adv. Synth. Catal. 2013, 355, 2115;
4. B. Yu, L.-N. He, ChemSusChem 2015, 8, 52;
5. M. Cokoja, C. Bruckmeier, B. Rieger, W. A. Herrmann, F. E. Kühn, Angew. Chem. Int. Ed. 2011, 50, 8510;
6. Angew. Chem. 2011, 123, 8662;
7. Y. Tsuji, T. Fujihara, Chem. Commun. 2012, 48, 9956.
8. X.-B. Lu, D. J. Darensbourg, Chem. Soc. Rev. 2012, 41, 1462;
9. R. Nakano, S. Ito, K. Nozaki, Nat. Chem. 2014, 6, 325;
10. M. R. Kember, C. K. Williams, J. Am. Chem. Soc. 2012, 134, 15676;
11. G. W. Coates, D. R. Moore, Angew. Chem. Int. Ed. 2004, 43, 6618;
12. Angew. Chem. 2004, 116, 6784; Formation of C-O bonds in linear/cyclic carbonates:
13. J. A. Kozak, J. Wu, X. Su, F. Simeon, T. A. Hatton, T. F. Jamison, J. Am. Chem. Soc. 2013, 135, 18497;
14. V. Laserna, G. Fiorani, C. J. Whiteoak, E. Martin, E. C. Escudero-Adán, A. W. Kleij, Angew. Chem. Int. Ed. 2014, 53, 10416;
15. Angew. Chem. 2014, 126, 10584;
16. W.-M. Ren, G.-P- Wu, F. Lin, J.-Y. Jiang, C. Liu, Y. Luo, X.-B. Lu, Chem. Sci. 2012, 3, 2094;
17. S. Yoshida, K. Fukui, S. Kikuchi, T. Yamada, J. Am. Chem. Soc. 2010, 132, 4072; Formation of C-N bonds to afford various products:
18. F. Fontana, C. C. Chen, V. K. Aggarwal, Org. Lett. 2011, 13, 3454;
19. O. Jacquet, C. Das Neves Gomes, M. Ephritikhine, T. Cantat, J. Am. Chem. Soc. 2012, 134, 2934;
20. K. Beydoun, G. Ghattas, K. Thenert, J. Klankermayer, W. Leitner, Angew. Chem. Int. Ed. 2014, 53, 11010;
21. Angew. Chem. 2014, 126, 11190;
22. Y. Li, T. Yan, K. Junge, M. Beller, Angew. Chem. Int. Ed. 2014, 53, 10476;
23. Angew. Chem. 2014, 126, 10644;
24. W.-J. Yoo, C.-J. Li, Adv. Synth. Catal. 2008, 350, 1503.
25. G. Centi, E. A. Quadrelli, S. Perathoner, Energy Environ. Sci. 2013, 6, 1711;
26. Carbon Dioxide as Chemical Feedstock (Ed.:, M. Aresta,), Wiley-VCH, Weinheim, 2010;
27. New and Future Developments in Catalysis: Activation of Carbon Dioxide (Ed.:, S. L. Suib,), Elsevier, Amsterdam, 2013.
28. 2. See:, C. Das Neves Gomes, O. Jacquet, C. Villiers, P. Thuéry, M. Ephritikhine, T. Cantat, Angew. Chem. Int. Ed. 2012, 51, 187;
29. Angew. Chem. 2012, 124, 191.
30. A. G. Myers, P. J. Proteau, T. M. Handel, J. Am. Chem. Soc. 1988, 110, 7212;
31. A. G. Myers, K. L. Widdowson, Tetrahedron Lett. 1988, 29, 6389;
32. P. Yan, X. Tan, H. Jing, S. Duan, X. Wang, Z. Liu, J. Org. Chem. 2011, 76, 2459;
33. J. A. H. Inkster, I. Ling, N. S. Honson, L. Jacquet, R. Gries, E. Plettner, Tetrahedron: Asymmetry 2005, 16, 3773.
34. Q.-W. Song, W.-Q. Chen, R. Ma, A. Yu, Q.-Y. Li, Y. Chang, L.-N. He, ChemSusChem 2015, 8, 821;
35. W. Yamada, Y. Sugawara, H. M. Cheng, T. Ikeno, T. Yamada, Eur. J. Org. Chem. 2007, 2604; see also Ref. [2h].
36. M. North, R. Pasquale, Angew. Chem. Int. Ed. 2009, 48, 2946;
37. Angew. Chem. 2009, 121, 2990;
38. A. Khan, R. Zheng, Y. Kan, J. Ye, J. Xiang, Y. Zhang, Angew. Chem. Int. Ed. 2014, 53, 6439;
39. Angew. Chem. 2014, 126, 6557;
40. C. J. Whiteoak, N. Kielland, V. Laserna, E. C. Escudero-Adán, E. Martin, A. W. Kleij, J. Am. Chem. Soc. 2013, 135, 1228;
41. W. Guo, J. González-Fabra, N. A. G. Bandeira, C. Bo, A. W. Kleij, Angew. Chem. Int. Ed. 2015, 54, 11686;
42. Angew. Chem. 2015, 127, 11852;
43. Y.-B. Wang, Y.-M. Wang, W.-Z. Zhang, X.-B. Lu, J. Am. Chem. Soc. 2013, 135, 11996.
44. C. M. Byrne, S. D. Allen, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2004, 126, 11404;
45. L. Peña Carrodeguas, J. González-Fabra, F. Castro-Gómez, C. Bo, A. W. Kleij, Chem. Eur. J. 2015, 21, 6115;
46. O. Hauenstein, M. Reiter, S. Agarwal, B. Rieger, A. Greiner, Green. Chem. 2016, 18, 760-770; Yoshida et al. reported on the use of propargylic alcohols to form highly substituted cyclic carbonates:
47. M. Yoshida, M. Fujita, T. Ishii, M. Ihara, J. Am. Chem. Soc. 2003, 125, 4874.
48. J. Rintjema, W. Guo, E. Martin, E. C. Escudero-Adán, A. W. Kleij, Chem. Eur. J. 2015, 21, 10754.
49. N. Ishida, Y. Shimamoto, M. Murakami, Angew. Chem. Int. Ed. 2012, 51, 11750;
50. Angew. Chem. 2012, 124, 11920;
51. S. Minakata, I. Sasaki, T. Ide, Angew. Chem. Int. Ed. 2010, 49, 1309;
52. Angew. Chem. 2010, 122, 1331;
53. B. A. Vara, T. J. Struble, W. Wang, M. Dobish, J. N. Johnston, J. Am. Chem. Soc. 2015, 137, 7302;
54. 2-mediated alcohol activation through alkyl carbonic acid formation and using it as a leaving group in intermolecular allylation chemistry. See:
55. S. B. Lang, T. M. Locascio, J. A. Tunge, Org. Lett. 2014, 16, 4308.
56. R. M. Hanson, Chem. Rev. 1991, 91, 437;
57. A. Riera, M. Moreno, Molecules 2010, 15, 1041; For synthesis of chiral epoxy alcohols see:
58. J. L. Olivares-Romero, Z. Li, H. Yamamoto, J. Am. Chem. Soc. 2013, 135, 3411;
59. C. Wang, H. Yamamoto, J. Am. Chem. Soc. 2014, 136, 1222. Epoxy amines can be simply derived from epoxy alcohols or by standard nucleophilic substitution using alcohol activating groups.
60. A. W. Miller, S. T. Nguyen, Org. Lett. 2004, 6, 2301;
61. Z.-Z. Yang, Y.-N. Li, Y.-Y. Wei, L.-N. He, Green Chem. 2011, 13, 2351.