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Green Chemistry
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Journal Name
ARTICLE
Earth-abundant element, with no risk of ore depletion even at
long term. Moreover, there was no need to add an elaborated,
expansive organic ligand to make it active in the cleavage
reaction. Finally, the process was highly efficient to open the
route to muconolactone compounds. Especially, catechols
obtained from lignin depolymerization were converted into
original muconolactones with good yields (>70%). They
represent a promising class of intermediates towards the
synthesis of compounds of interest, while allowing the
valorization of lignin depolymerization products in an efficient
fashion.
1541.
DOI: 10.1039/D0GC02157A
23 Y. Deng, L. Ma and Y. Mao, Biochem.Eng. J., 2016, 105, 16–26.
24 N. S. Kruyer and P. Peralta-Yahya, Curr. Opin. Biotech., 2017, 45, 136–143.
25 N.-Z. Xie, H. Liang, R.-B. Huang and P. Xu, Biotechnol. Adv., 2014, 32, 615–622.
26 D. H. Jo, Y. M. Chiou and L. Que Jr., Inorg. Chem., 2001, 40, 3181–3190.
27 R. Yamahara, S. Ogo, H. Masuda and Y. Watanabe, J. Inorg. Biochem., 2002, 88,
284–294.
28 R. Viswanathan, M. Palaniandavar, T. Balasubramanian and T. P. Muthiah,
Inorg. Chem., 1998, 37, 2943–2951.
29 W. O. Koch and H. J. Krüger, Angew. Chem. Int. Ed. Engl, 1996, 34, 2671–2674.
30 D. D. Cox and L. Que Jr., J. Am. Chem. Soc., 1988, 110, 8085–8092.
31 R. Jastrzebski, E. J. V. D. Berg, B. M. Weckhuysen and P. C. A. Bruijnincx, Catal.
Sci. Technol., 2015, 5, 2103–2109.
32 H. G. Jang, D. D. Cox and L. Que Jr., J. Am. Chem. Soc., 1991, 113, 9200–9204.
33 H. Klenk, P. H. Götz, R. Siegmeier and W. Mayr, in Ullmann's Encyclopedia of
Industrial Chemistry, ed. Wiley-VCH, Weinheim, 6th edition, 2005, Peroxy
compounds, organic.
34 A. J. Pandell, J. Org. Chem.,1976, 41, 3992–3996.
35 A. J. Pandell, J. Org. Chem., 1983, 48, 3908–3912.
36 Y. Hitomi, H. Yoshida, T. Tanaka and T. Funabiki, J. Mol. Catal. A: Chem., 2006,
251, 239–245.
37 A. J. Pandell and W. E. Matras, J. Org. Chem., 1987, 52, 697–699.
38 X.-B. Zhao, T. Zhang, Y.-J. Zhou and D.-H. Liu, Chin. J. Proc. Eng., 2008, 8, 35-41.
39 A. Wacek, H. Frederiksen, US2534212, 1950.
Conflicts of interest
There are no conflicts to declare.
40 S. Leveneur, M. Thönes, J.-P. Hébert, B. Taouk and T. Salmi, Indus. Eng. Chem.
Res., 2012, 51, 13999–14007.
41 B. Guicheret, Y. Bertholo, P. Blach, Y. Raoul, E. Métay and M. Lemaire,
ChemSusChem, 2018, 11, 3431–3437.
42 P. D. Filippis, M. Scarsella and N. Verdone, Indus. Eng. Chem. Res., 2009, 48,
1372–1375.
43 E. Santacesaria, V. Russo, R. Tesser, R. Turco and M. D. Serio, Indus. Eng. Chem.
Res., 2017, 56, 12940–12952.
44 D. A. Bulushev and J. R. H. Ross, ChemSusChem, 2018, 11, 821–836.
45 J. Bomon, E. V. D. Broeck, M. Bal, Y. Liao, S. Sergeyev, V. V. Speybroeck, B. F.
Sels and B. U. W. Maes, Angew. Chem. Int. Ed., 2020, 59, 3063–3068.
46 L. Yang, W. Zhou, K. Seshan and Y. Li, J. Mol. Catal. A: Chem., 2013, 368-369, 61–
65.
Acknowledgements
We thank the Université de Rennes 1, the Centre National de la
Recherche Scientifique (CNRS), the Région Bretagne, and the ANR
labcom program (17-LCV2-0009-01). F. C. thanks the ANRT for a
CIFRE PhD grant and Rennes Metropole council for a mobility grant.
47 L. Yang, Y. Li and P. E. Savage, Indus. Eng. Chem. Res., 2014, 53, 2633–2639.
48 J. Tian, C. Yi, Z. He, M. Yao and D. Sang, ChemistrySelect, 2017, 2, 9211–9214.
49 F. Chen, Y. Tobimatsu, D. Havkin-Frenkel, R. A. Dixon and J. Ralph, PNAS, 2012,
109, 1772–1777.
50 M. L. Stone, E. M. Anderson, K. M. Meek, M. Reed, R. Katahira, F. Chen, R. A.
Dixon, G. T. Beckham and Y. Román-Leshkov, ACS Sust. Chem. Eng., 2018, 6,
11211–11218.
51 Y. Li, L. Shuai, H. Kim, A. H. Motagamwala, J. K. Mobley, F. Yue, Y. Tobimatsu, D.
Havkin-Frenkel, F. Chen, R. A. Dixon, J. S. Luterbacher, J. A. Dumesic and J. Ralph,
Sci. Adv., 2018, 4, eaau2968.
52 Y. Tobimatsu, F. Chen, J. Nakashima, L. L. Escamilla-Treviño, L. Jackson, R. A.
Dixon and J. Ralph, Plant Cell, 2013, 25, 2587–2600.
Notes and references
1
2
Y. Lu, Y.-C. Lu, H.-Q. Hu, F.-J. Xie, X.-Y. Wei and X. Fan, J. Spectrosc., 2017, 1–15.
W. Schutyser, T. Renders, S. V. den Bosch, S.-F. Koelewijn, G. T. Beckham and B.
F. Sels, Chem. Soc. Rev., 2018, 47, 852–908.
3
L. Cao, I. K. M. Yu, Y. Liu, X. Ruan, D. C. W. Tsang, A. J. Hunt, Y. S. Ok, H. Song and
S. Zhang, Bioresour. Technol., 2018, 269, 465–475.
4
5
C. Liu, S. Wu, H. Zhang and R. Xiao, Fuel Proc. Technol., 2019, 191, 181–201.
K. Barta, G. R. Warner, E. S. Beach and P. T. Anastas, Green Chem., 2014, 16,
191–196.
6
D. R. Vardon, N. A. Rorrer, D. Salvachúa, A. E. Settle, C. W. Johnson, M. J.
Menart, N. S. Cleveland, P. N. Ciesielski, K. X. Steirer, J. R. Dorgan and G. T.
Beckham, Green Chem., 2016, 18, 3397–3413.
53 S. Wang, S. Su, L.-P. Xiao, B. Wang, R.-C. Sun and G. Song, ACS Sust. Chem. Eng.,
2020, 8, 7031–7038.
54 J.-L. Dubois, Arkema France, WO2013/011226A1, 2013.
55 L. Berg, K. M. Wendt and R. J. Szabados, US 5006205, 1991.
56 K. Rauch, H. Kiefer, D. Hesse, M. Strohmeyer and H. Hohenschutz, BASF
Aktiengesellschaft, US 3983010, 1976.
7
J. M. Carraher, T. Pfennig, R. G. Rao, B. H. Shanks and J. P. Tessonnier, Green
Chem., 2017, 19, 3042–3050.
L. Coudray, J. W. Frost and D. Schweitzer, Amyris, Inc., US 2013/0085255A1, 2013.
8
9
N. A. Rorrer, J. R. Dorgan, D. R. Vardon, C. R. Martinez, Y. Yang and G. T.
Beckham, ACS Sust. Chem. Eng., 2016, 4, 6867–6876.
10 J. L. Milan, M. Mang and C. Ozmer-Al, Myriant Corp., WO 2016/069411A1, 2016.
11 G. Quintens, J. H. Vrijsen, P. Adriaensens, D. Vanderzande and T. Junkers, Polym.
Chem., 2019, 10, 5555–5563.
12 J. E. Matthiesen, J. M. Carraher, M. Vasiliu, D. A. Dixon and J. P. Tessonnier, ACS
Sust. Chem. Eng., 2016, 4, 3575–3585.
13 J. S. Pierre, L. Duran and A. V. Heiningen, J. Anal. Appl. Pyrol., 2015, 113, 591–
598.
14 M. Suastegui, J. E. Matthiesen, J. M. Carraher, N. Hernandez, N. R. Quiroz, A.
Okerlund, E. W. Cochran, Z. Shao and J.-P. Tessonnier, Angew. Chem. Int. Ed.,
2016, 55, 2368–2373.
15 M. Giurg, E. Kowal, H. Muchalski, L. Syper and J. Młochowski, Synth. Commun.,
2009, 39, 251–266.
16 V. S. Sobolev, S. T. Deyrup and J. B. Gloer, J. Agr. Food Chem., 2006, 54, 2111–
2115.
17 A. Skiba, V. Hecht and D. H. Pieper, J. Bacteriol, 2002, 184, 5402–5409.
18 J. Huo, Z. Hu, D. Chen, S. Luo, Z. Wang, Y. Gao, M. Zhang and H. Chen, ACS
Omega, 2017, 2, 5557–5564.
19 P. Fan, H. Lou, W. Yu, D. Ren, B. Ma and M. Ji, Tetrahedron Lett., 2004, 45, 3163–
3166.
20 R. Miyano, H. Matsuo, K. Nonaka, T. Mokudai, Y. Niwano, K. Shiomi, Y.
Takahashi, S. Ōmura and T. Nakashima, J. Biosci. Bioeng., 2018, 126, 661–666.
21 B. H. Shanks and P. L. Keeling, Green Chem., 2017, 19, 3177–3185.
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