Catalyst Development in the Context of Ring Expansion–Addition of Carbon Dioxide to Epoxides to Give Organic Carbonates

Christopher J. Whiteoak; Arjan W. Kleij

doi:10.1055/s-0033-1339483

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(14): 1748-1756
DOI: 10.1055/s-0033-1339483

account

Catalyst Development in the Context of Ring Expansion–Addition of Carbon Dioxide to Epoxides to Give Organic Carbonates

Christopher J. Whiteoak

^aInstitute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain Fax: +34(977)920828 eMail: akleij@iciq.es

,

Arjan W. Kleij*

^aInstitute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain Fax: +34(977)920828 eMail: akleij@iciq.es

^bCatalan Institute for Research and Advanced Studies (ICREA), Pg. Lluis Companys 23, 08010 Barcelona, Spain

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Abstract

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Dedicated to Prof. Javier de Mendoza for his contributions to chemical science

Abstract

In the last decade, chemists have increasingly focused on the development of new and more efficient methods for the catalytic conversion of carbon dioxide into value-added organic molecules. Homogeneous catalysis has proved to be a key technology for the conversion of carbon dioxide under particularly mild reaction conditions that meet the increasing societal demands for sustainable chemical processing. In this account article, we focus on the most effective routes developed for ring expansion–addition reaction of carbon dioxide to epoxides mediated by either metal catalysts or organocatalyst systems to give cyclic organic carbonates.

1 Introduction

2 Metal-Mediated Synthesis of Cyclic Organic Carbonates

3 Organocatalyzed Formation of Cyclic Organic Carbonates

4 Mechanistic Considerations

5 Concluding Remarks

Key words

epoxides - homogeneous catalysis - Lewis acids - ring expansion - Schiff bases - carbonates - heterocycles

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Referenzen

References

For selected reviews/books on this topic, see:

1a Martin R, Kleij AW. ChemSusChem 2011; 4: 1259
1b Bruckmeier C, Rieger B, Herrmann WA, Kühn FE. Angew. Chem. Int. Ed. 2011; 50: 8510
1c Carbon Dioxide as Chemical Feedstock . Aresta M. Wiley-VCH; Weinheim: 2010
1d Lu X.-B, Ren W.-M, Wu G.-P. Acc. Chem. Res. 2012; 45: 1721

For some recent examples, see:

2a Gomes CD. N, Jacquet O, Villiers C, Thuéry P, Ephritikhine M, Cantat T. Angew. Chem. Int. Ed. 2012; 51: 187
2b Langer R, Diskin-Posner Y, Leitus G, Shimon LJ. W, Ben-David Y, Milstein D. Angew. Chem. Int. Ed. 2011; 50: 9948

For examples of carbon dioxide addition chemistry, see:

3a Yoshida M, Fujita M, Ishii T, Ihara M. J. Am. Chem. Soc. 2003; 125: 4874
3b Jeske RC, Rowley JM, Coates GW. Angew. Chem. Int. Ed. 2008; 47: 6041
3c Darensbourg DJ, Wilson SJ. J. Am. Chem. Soc. 2011; 133: 18610
3d Takimoto M, Mori M. J. Am. Chem. Soc. 2004; 126: 5956
3e Li S, Yuan W, Ma S. Angew. Chem. Int. Ed. 2011; 50: 2578

For recent reviews, see:

4a Decortes A, Castilla AM, Kleij AW. Angew. Chem. Int. Ed. 2010; 49: 9822
4b Pescarmona PP, Taherimehr M. Catal. Sci. Technol. 2012; 2: 2169
4c North M, Pasquale R, Young C. Green Chem. 2010; 12: 1514

5 The term ‘cycloaddition’ that is generally used for this transformation is, in our view, incorrect as ‘cycloaddition’ officially refers to a pericyclic chemical conversion between one or more unsaturated molecules. This combination should then give a cyclic product with a net reduction in bond multiplicity. We feel that a better description of the addition of CO₂ to epoxides would be ‘ring expansion–addition’.
6 Ema, Sakai, and co-workers recently communicated a bifunctional porphyrin-based metal catalyst that shows very high turnover frequencies and turnover numbers, see: Ema T, Miyazaki Y, Koyama S, Yano Y, Sakai T. Chem. Commun. (Cambridge) 2012; 48: 4489

There are only a few reports of effective conversions of epoxides and CO₂ into cyclic carbonates under ambient conditions; see for example:

7a Clegg W, Harrington RW, North M, Pasquale R. Chem. Eur. J. 2010; 16: 6828
7b Decortes A, Kleij AW. ChemCatChem 2011; 3: 831

8 The increased use of computational methods in this and related areas of CO₂ catalysis is a recent trend, see: Drees M, Cokoja M, Kühn FE. ChemCatChem 2012; 4: 1703

For selected contributions, see:

9a Darensbourg DJ, Moncada AI, Choi W, Reibenspies JH. J. Am. Chem. Soc. 2008; 130: 6523
9b Darensbourg DJ, Moncada AI. Macromolecules 2010; 43: 5996

For some selected examples, see:

10a Salassa G, Coenen MJ. J, Wezenberg SJ, Hendriksen BL. M, Speller S, Elemans JA. A. W, Kleij AW. J. Am. Chem. Soc. 2012; 134: 7186
10b Wezenberg SJ, Salassa G, Escudero-Adán EC, Benet-Buchholz J, Kleij AW. Angew. Chem. Int. Ed. 2011; 50: 713

11 Decortes A, Martínez Belmonte M, Benet-Buchholz J, Kleij AW. Chem. Commun. (Cambridge) 2010; 46: 4580
12 Kleij AW, Tooke DM, Kuil M, Lutz M, Spek AL, Reek JN. H. Chem. Eur. J. 2005; 11: 4743
13 Taherimehr M, Decortes A, Al-Amsyar S.-M, Lueangchaichaweng W, Whiteoak CJ, Kleij AW, Pescarmona PP. Catal. Sci. Technol. 2012; 2: 2231
14 Escárcega-Bobadilla MV, Salassa G, Martínez Belmonte M, Escudero-Adán EC, Kleij AW. Chem. Eur. J. 2012; 18: 6805
15 Wezenberg SJ, Escudero-Adán EC, Benet-Buchholz J, Kleij AW. Chem. Eur. J. 2009; 15: 5695
16 Escárcega-Bobadilla MV, Martínez Belmonte M, Martin E, Escudero-Adán EC, Kleij AW. Chem. Eur. J. 2013; 19: 2641
17 Licini G, Mba M, Zonta C. Dalton Trans. 2009; 5265
18 Whiteoak CJ, Gjoka B, Martin E, Martínez Belmonte M, Escudero-Adán EC, Zonta C, Licini G, Kleij AW. Inorg. Chem. 2012; 51: 10639
19 Whiteoak CJ, Martin E, Martínez Belmonte M, Benet-Buchholz J, Kleij AW. Adv. Synth. Catal. 2012; 354: 469

For some other example, see:

20a Li C.-Y, Wu C.-R, Liu Y.-C, Ko B.-T. Chem. Commun. (Cambridge) 2012; 48: 9628
20b See ref. 9 for oxetane conversion.

21 Whiteoak CJ, Martin E, Escudero-Adán EC, Kleij AW. Adv. Synth. Catal. 2013; 355 DOI: 10.1002/adsc.201201070

For some examples, see:

22a Wu G.-P, Wei S.-H, Ren W.-M, Lu X.-B, Xu T.-Q, Darensbourg DJ. J. Am. Chem. Soc. 2011; 133: 15191
22b Wu G.-P, Wei S.-H, Lu X.-B, Ren W.-M, Darensbourg DJ. Macromolecules 2010; 43: 9202

23 Raders SM, Verkade JG. J. Org. Chem. 2009; 74: 5417
24 Whiteoak CJ, Kielland N, Laserna V, Escudero-Adán EC, Martin E, Kleij AW. J. Am. Chem. Soc. 2013; 135: 1228
25 Chatelet B, Joucla L, Dutasta J.-P, Martinez A, Szeto KC, Dufaud V. J. Am. Chem. Soc. 2013; 135: 5348

26a Kawanami H, Sasaki A, Matsuia K, Ikushima Y. Chem. Commun. (Cambridge) 2003; 896
26b Yang Z.-Z, He L.-N, Miao C.-X, Chanfreau S. Adv. Synth. Catal. 2010; 352: 2233
26c Yang Z.-Z, Zhao Y.-N, He L.-N, Gao J, Yin Z.-S. Green Chem. 2012; 14: 519
26d Zhang Y, Yin S, Luo S, Au CT. Ind. Eng. Chem. Res. 2012; 51: 3951
26e Aprile C, Giacalone F, Agrigento P, Liotta LF, Martens JA, Pescarmona PP, Gruttadauria M. ChemSusChem 2011; 4: 1830
26f Sun J, Wang J, Cheng W, Zhang J, Li X, Zhang S, She Y. Green Chem. 2012; 14: 654
26g Foltran S, Alsarraf J, Robert F, Landais Y, Cloutet E, Cramail H, Tassaing T. Catal. Sci. Technol. 2013; 3: 1046
26h Tharun J, Mathai G, Roshan R, Kathalikkattil AC, Bomi K, Park D.-W. Phys. Chem. Chem. Phys. 2013; 15: 9029

27 Zhou H, Zhang W.-Z, Liu C.-H, Qu J.-P, Lu X.-B. J. Org. Chem. 2008; 73: 8039
28 He L.-N, Yasuda H, Sakakura T. Green Chem. 2003; 5: 92
29 Sit WN, Ng SM, Kwong KY, Lau CP. J. Org. Chem. 2005; 70: 8583
30 Tsutsumi Y, Yamakawa K, Yoshida M, Ema T, Sakai T. Org. Lett. 2010; 12: 5728
31 Qi C, Ye J, Zeng W, Ziang H. Adv. Synth. Catal. 2010; 352: 1925
32 Shen Y.-M, Duan W.-L, Shi M. Adv. Synth. Catal. 2003; 345: 337
33 Spencer JN, Heckman RA, Harner RS, Shoop SL, Robertson KS. J. Phys. Chem. 1973; 77: 3103
34 Whiteoak CJ, Nova A, Maseras F, Kleij AW. ChemSusChem 2012; 5: 2032

For relevant mechanistic work related to cyclic carbonate synthesis, see:

35a North M, Pasquale R. Angew. Chem. Int. Ed. 2009; 48: 2946
35b Wang J.-Q, Dong K, Cheng W.-G, Sun J, Zhang SJ. Catal. Sci. Technol. 2012; 2: 1480
35c Ma J, Liu J, Zhang Z, Han B. Green Chem. 2012; 14: 2410
35d Jutz F, Andanson JM, Baiker A. Chem. Rev. 2011; 111: 322

36 Castro-Gómez F, Salassa G, Kleij AW, Bo C. Chem. Eur. J. 2013; 19: 6289