Vortex Fluidic Ethenolysis, Integrating a Rapid Quench of Ruthenium Olefin Metathesis Catalysts
Scott J. Pye A , Justin M. Chalker A B and Colin L. Raston A BA Flinders Institute for Nanoscale Science and Technology, College of Science and Engineering, Flinders University, Bedford Park, SA 5042, Australia.
B Corresponding authors. Email: justin.chalker@flinders.edu.au; colin.raston@flinders.edu.au
Australian Journal of Chemistry 73(12) 1138-1143 https://doi.org/10.1071/CH20005
Submitted: 6 January 2020 Accepted: 29 April 2020 Published: 26 June 2020
Abstract
Ruthenium-catalysed ethenolysis occurs in a vortex fluidic device (VFD) – a scalable, thin-film microfluidic continuous flow process. This process takes advantage of the efficient mass transfer of gaseous reagents into the dynamic thin film of liquid. Also reported is the rapid quenching of the ruthenium-based olefin metathesis catalyst by the addition of a saturated solution of N-acetyl-l-cysteine in MeCN, as a convenient alternative to previously reported quenching methods.
References
[1] A. H. Hoveyda, A. R. Zhugralin, Nature 2007, 450, 243.| Crossref | GoogleScholarGoogle Scholar | 17994091PubMed |
[2] T. P. J. Montgomery, M. Adam, R. H. Grubbs, Catalysts 2017, 7, 2073.
[3] O. M. Ogba, N. C. Warner, D. J. O’Leary, R. H. Grubbs, Chem. Soc. Rev. 2018, 47, 4510.
| Crossref | GoogleScholarGoogle Scholar | 29714397PubMed |
[4] J. Bidange, C. Fischmeister, C. Bruneau, Chem. – Eur. J. 2016, 22, 12226.
| Crossref | GoogleScholarGoogle Scholar | 27359344PubMed |
[5] J. Spekreijse, J. P. M. Sanders, J. H. Bitter, E. L. Scott, ChemSusChem 2017, 10, 470.
| Crossref | GoogleScholarGoogle Scholar | 27860333PubMed |
[6] S. L. Mangold, R. H. Grubbs, Chem. Sci. 2015, 6, 4561.
| Crossref | GoogleScholarGoogle Scholar | 26509000PubMed |
[7] S. C. Marinescu, D. S. Levine, Y. Zhao, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2011, 133, 11512.
| Crossref | GoogleScholarGoogle Scholar | 21718001PubMed |
[8] V. M. Marx, M. B. Herbert, B. K. Keitz, R. H. Grubbs, J. Am. Chem. Soc. 2013, 135, 94.
| Crossref | GoogleScholarGoogle Scholar | 23244210PubMed |
[9] H. Miyazaki, M. B. Herbert, P. Liu, X. Dong, X. Xu, B. K. Keitz, T. Ung, G. Mkrtumyan, K. N. Houk, R. H. Grubbs, J. Am. Chem. Soc. 2013, 135, 5848.
| Crossref | GoogleScholarGoogle Scholar | 23547887PubMed |
[10] C. Bruneau, C. Fischmeister, D. Mandelli, W. A. Carvalho, E. N. dos Santos, P. H. Dixneuf, L. S. Fernandes, Catal. Sci. Technol. 2018, 8, 3989.
| Crossref | GoogleScholarGoogle Scholar |
[11] K. A. Burdett, L. D. Harris, P. Margl, B. R. Maughon, T. Mokhtar-Zadeh, P. C. Saucier, E. P. Wasserman, Organometallics 2004, 23, 2027.
| Crossref | GoogleScholarGoogle Scholar |
[12] L. M. de Espinosa, M. A. R. Meier, in Olefin Metathesis of Renewable Platform Chemicals (Eds M. A. R. Meier, B. M. Weckhuysen, P. C. A. Bruijnincx) 2012, pp. 1–44 (Springer: Berlin).
[13] R. W. Jenkins, L. A. Sargeant, F. M. Whiffin, F. Santomauro, D. Kaloudis, P. Mozzanega, C. D. Bannister, S. Baena, C. J. Chuck, ACS Sustain. Chem.& Eng. 2015, 3, 1526.
| Crossref | GoogleScholarGoogle Scholar |
[14] B. B. Marvey, Int. J. Mol. Sci. 2008, 9, 1393.
| Crossref | GoogleScholarGoogle Scholar | 19325810PubMed |
[15] M. A. R. Meier, J. O. Metzger, U. S. Schubert, Chem. Soc. Rev. 2007, 36, 1788.
| Crossref | GoogleScholarGoogle Scholar |
[16] J. C. Mol, Top. Catal. 2004, 27, 97.
| Crossref | GoogleScholarGoogle Scholar |
[17] S. Wolf, H. Plenio, Green Chem. 2011, 13, 2008.
| Crossref | GoogleScholarGoogle Scholar |
[18] A.-M. Aguirre, A. Bassi, P. Saxena, Crit. Rev. Biotechnol. 2013, 33, 293.
| Crossref | GoogleScholarGoogle Scholar | 22804334PubMed |
[19] J. Esteban, M. Ladero, J. Food Sci. Technol. 2018, 53, 1095.
| Crossref | GoogleScholarGoogle Scholar |
[20] Y. J. Su, K. H. Song, P. D. Zhang, Y. Q. Su, J. Cheng, X. Chen, Renew. Sustain. Energy Rev. 2017, 74, 402.
| Crossref | GoogleScholarGoogle Scholar |
[21] D. R. Anderson, T. Ung, G. Mkrtumyan, G. Bertrand, R. H. Grubbs, Y. Schrodi, Organometallics 2008, 27, 563.
| Crossref | GoogleScholarGoogle Scholar | 18584055PubMed |
[22] N. W. Awang, K. Tsutsumi, B. Huštáková, S. F. M. Yusoff, K. Nomura, B. M. Yamin, RSC Adv. 2016, 6, 100925.
| Crossref | GoogleScholarGoogle Scholar |
[23] A. K. Chatterjee, T.-L. Choi, D. P. Sanders, R. H. Grubbs, J. Am. Chem. Soc. 2003, 125, 11360.
| Crossref | GoogleScholarGoogle Scholar | 16220959PubMed |
[24] S. Gutierras, S. M. Vargas, M. A. Tlenkopatchev, J. Chem. Thermodyn. 2004, 36, 29.
| Crossref | GoogleScholarGoogle Scholar |
[25] L. M. Kustov, D. B. Furman, J. Organomet. Chem. 2018, 867, 261.
| Crossref | GoogleScholarGoogle Scholar |
[26] M. S. Sanford, J. A. Love, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 6543.
| Crossref | GoogleScholarGoogle Scholar | 11439041PubMed |
[27] R. M. Thomas, B. K. Keitz, T. M. Champagne, R. H. Grubbs, J. Am. Chem. Soc. 2011, 133, 7490.
| Crossref | GoogleScholarGoogle Scholar | 21510645PubMed |
[28] P. S. Engl, C. B. Santiago, C. P. Gordon, W.-C. Liao, A. Fedorov, C. Copéret, M. S. Sigman, A. Togni, J. Am. Chem. Soc. 2017, 139, 13117.
| Crossref | GoogleScholarGoogle Scholar | 28820588PubMed |
[29] P. Wyrębek, P. Małecki, A. Sytniczuk, W. Kośnik, A. Gawin, J. Kostrzewa, A. Kajetanowicz, K. Grela, ACS Omega 2018, 3, 18481.
| Crossref | GoogleScholarGoogle Scholar | 31458420PubMed |
[30] S. Byun, H. Seo, J.-H. Choi, J. Y. Ryu, J. Lee, W.-j. Chung, S. Hong, Organometallics 2019, 38, 4121.
| Crossref | GoogleScholarGoogle Scholar |
[31] G. S. Forman, R. M. Bellabarba, R. P. Tooze, A. M. Z. Slawin, R. Karch, R. Winde, J. Organomet. Chem. 2006, 691, 5513.
| Crossref | GoogleScholarGoogle Scholar |
[32] J. Julis, S. A. Bartlett, S. Baader, N. Beresford, E. J. Routledge, C. S. J. Cazin, D. J. Cole-Hamilton, Green Chem. 2014, 16, 2846.
| Crossref | GoogleScholarGoogle Scholar |
[33] R. Kadyrov, C. Azap, S. Weidlich, D. Wolf, Top. Catal. 2012, 55, 538.
| Crossref | GoogleScholarGoogle Scholar |
[34] A. Kajetanowicz, M. Chwalba, A. Gawin, A. Tracz, K. Grela, Eur. J. Lipid Sci. Technol. 2019, 122, 1900263.
| Crossref | GoogleScholarGoogle Scholar |
[35] D. Mandelli, M. J. D. M. Jannini, R. Buffon, U. Schuchardt, J. Am. Oil Chem. Soc. 1996, 73, 229.
| Crossref | GoogleScholarGoogle Scholar |
[36] S. C. Marinescu, R. R. Schrock, P. Müller, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 10840.
| Crossref | GoogleScholarGoogle Scholar | 19618951PubMed |
[37] V. M. Marx, A. H. Sullivan, M. Melaimi, S. C. Virgil, B. K. Keitz, D. S. Weinberger, G. Bertrand, R. H. Grubbs, Angew. Chem. Int. Ed. 2015, 54, 1919.
| Crossref | GoogleScholarGoogle Scholar |
[38] Y. Schrodi, T. Ung, A. Vargas, G. Mkrtumyan, C. W. Lee, T. M. Champagne, R. L. Pederson, S. H. Hong, Clean 2008, 36, 669.
| Crossref | GoogleScholarGoogle Scholar |
[39] M. B. Plutschack, B. Pieber, K. Gilmore, P. H. Seeberger, Chem. Rev. 2017, 117, 11796.
| Crossref | GoogleScholarGoogle Scholar | 28570059PubMed |
[40] H. P. L. Gemoets, Y. Su, M. Shang, V. Hessel, R. Luque, T. Noel, Chem. Soc. Rev. 2016, 45, 83.
| Crossref | GoogleScholarGoogle Scholar |
[41] A. Günther, K. F. Jensen, Lab Chip 2006, 6, 1487.
| Crossref | GoogleScholarGoogle Scholar | 17203152PubMed |
[42] R. L. Hartman, J. P. McMullen, K. F. Jensen, Angew. Chem. Int. Ed. 2011, 50, 7502.
| Crossref | GoogleScholarGoogle Scholar |
[43] B. Gutmann, D. Cantillo, C. O. Kappe, Angew. Chem. Int. Ed. 2015, 54, 6688.
| Crossref | GoogleScholarGoogle Scholar |
[44] M. Movsisyan, E. I. P. Delbeke, J. K. E. T. Berton, C. Battilocchio, S. V. Ley, C. V. Stevens, Chem. Soc. Rev. 2016, 45, 4892.
| Crossref | GoogleScholarGoogle Scholar | 27453961PubMed |
[45] J. Britton, K. A. Stubbs, G. A. Weiss, C. L. Raston, Chem. – Eur. J. 2017, 23, 13270.
| Crossref | GoogleScholarGoogle Scholar | 28597512PubMed |
[46] K. A. Alexander, E. A. Paulhus, G. M. L. Lazarus, N. E. Leadbeater, J. Organomet. Chem. 2016, 812, 74.
| Crossref | GoogleScholarGoogle Scholar |
[47] S. Monfette, M. Eyholzer, D. M. Roberge, D. E. Fogg, Chem. – Eur. J. 2010, 16, 11720.
| Crossref | GoogleScholarGoogle Scholar | 20821763PubMed |
[48] C. P. Park, M. M. Van Wingerden, S.-Y. Han, D.-P. Kim, R. H. Grubbs, Org. Lett. 2011, 13, 2398.
| Crossref | GoogleScholarGoogle Scholar | 21456591PubMed |
[49] D. D. Plaza, V. Strobel, P. K. K. S. Heer, A. B. Sellars, S.-S. Hoong, A. J. Clark, A. A. Lapkin, J. Chem. Technol. Biotechnol. 2017, 92, 2254.
| Crossref | GoogleScholarGoogle Scholar | 28919656PubMed |
[50] C. Schotten, D. Plaza, S. Manzini, S. P. Nolan, S. V. Ley, D. L. Browne, A. Lapkin, ACS Sustain. Chem. & Eng. 2015, 3, 1453.
| Crossref | GoogleScholarGoogle Scholar |
[51] C. Thurier, C. Fischmeister, C. Bruneau, H. Olivier-Bourbigou, P. H. Dixneuf, ChemSusChem 2008, 1, 118.
| Crossref | GoogleScholarGoogle Scholar | 18605674PubMed |
[52] N. A. Lundquist, M. J. Sweetman, K. R. Scroggie, M. J. H. Worthington, L. J. Esdaile, S. F. K. Alboaiji, S. E. Plush, J. D. Hayball, J. M. Chalker, ACS Sustain. Chem. & Eng. 2019, 7, 11044.
| Crossref | GoogleScholarGoogle Scholar |
[53] N. A. Lundquist, M. J. H. Worthington, N. Adamson, C. T. Gibson, M. R. Johnston, A. V. Ellis, J. M. Chalker, RSC Adv. 2018, 8, 1232.
| Crossref | GoogleScholarGoogle Scholar |
[54] M. J. H. Worthington, C. J. Shearer, L. J. Esdaile, J. A. Campbell, C. T. Gibson, S. K. Legg, Y. Yin, N. A. Lundquist, J. R. Gascooke, I. S. Albuquerque, J. G. Shapter, G. G. Andersson, D. A. Lewis, G. J. L. Bernardes, J. M. Chalker, Adv. Sustainable Syst. 2018, 2, 1800024.
| Crossref | GoogleScholarGoogle Scholar |
[55] R. Gawin, A. Kozakiewicz, P. A. Guńka, P. Dąbrowski, K. Skowerski, Angew. Chem. Int. Ed. 2017, 56, 981.
| Crossref | GoogleScholarGoogle Scholar |
[56] S. J. Pye, S. J. Dalgarno, J. M. Chalker, C. L. Raston, Green Chem. 2018, 20, 118.
| Crossref | GoogleScholarGoogle Scholar |
[57] J. Britton, C. L. Raston, RSC Adv. 2015, 5, 2276.
| Crossref | GoogleScholarGoogle Scholar |
[58] E. K. Sitepu, K. Corbin, X. Luo, S. J. Pye, Y. Tang, S. C. Leterme, K. Heimann, C. L. Raston, W. Zhang, Bioresour. Technol. 2018, 266, 488.
| Crossref | GoogleScholarGoogle Scholar | 29990765PubMed |
[59] L. A. Arrua, B. J. McCoy, J. M. Smith, Chem. Eng. Process. 1990, 36, 1768.
[60] D. L. Nascimento, A. Gawin, R. Gawin, P. A. Guńka, J. Zachara, K. Skowerski, D. E. Fogg, J. Am. Chem. Soc. 2019, 141, 10626.
| Crossref | GoogleScholarGoogle Scholar | 31248254PubMed |
[61] Y. M. Ahn, K. Yang, G. I. Georg, Org. Lett. 2001, 3, 1411.
| Crossref | GoogleScholarGoogle Scholar | 11348247PubMed |
[62] J. M. Blacquiere, T. Jurca, J. Weiss, D. E. Fogg, Adv. Synth. Catal. 2008, 350, 2849.
| Crossref | GoogleScholarGoogle Scholar |
[63] J. H. Cho, B. M. Kim, Org. Lett. 2003, 5, 531.
| Crossref | GoogleScholarGoogle Scholar | 12583761PubMed |
[64] P. G. Gassman, T. H. Johnson, J. Am. Chem. Soc. 1976, 98, 6055.
| Crossref | GoogleScholarGoogle Scholar |
[65] W. Liu, P. J. Nichols, N. Smith, Tetrahedron Lett. 2009, 50, 6103.
| Crossref | GoogleScholarGoogle Scholar |
[66] K. McEleney, D. P. Allen, A. E. Holliday, C. M. Crudden, Org. Lett. 2006, 8, 2663.
| Crossref | GoogleScholarGoogle Scholar | 16774226PubMed |
[67] L. A. Paquette, J. D. Schloss, I. Efremov, F. Fabris, F. Gallou, J. Méndez-Andino, J. Yang, Org. Lett. 2000, 2, 1259.
| Crossref | GoogleScholarGoogle Scholar | 10810722PubMed |
[68] A. Roy, M. A. Silvestri, R. A. Hall, S. D. Lepore, Tetrahedron Lett. 2017, 58, 106.
| Crossref | GoogleScholarGoogle Scholar | 28642627PubMed |
[69] N. K. Yee, V. Farina, I. N. Houpis, N. Haddad, R. P. Frutos, F. Gallou, X.-j. Wang, X. Wei, R. D. Simpson, X. Feng, V. Fuchs, Y. Xu, J. Tan, L. Zhang, J. Xu, L. L. Smith-Keenan, J. Vitous, M. D. Ridges, E. M. Spinelli, M. Johnson, K. Donsbach, T. Nicola, M. Brenner, E. Winter, P. Kreye, W. Samstag, J. Org. Chem. 2006, 71, 7133.
| Crossref | GoogleScholarGoogle Scholar | 16958506PubMed |
[70] B. R. Galan, K. P. Kalbarczyk, S. Szczepankiewicz, J. B. Keister, S. T. Diver, Org. Lett. 2007, 9, 1203.
| Crossref | GoogleScholarGoogle Scholar | 17326645PubMed |
[71] G. Szczepaniak, A. Ruszczyńska, K. Kosiński, E. Bulska, K. Grela, Green Chem. 2018, 20, 1280.
| Crossref | GoogleScholarGoogle Scholar |
[72] G. Szczepaniak, K. Urbaniak, C. Wierzbicka, K. Kosiński, K. Skowerski, K. Grela, ChemSusChem 2015, 8, 4139.
| Crossref | GoogleScholarGoogle Scholar | 26556779PubMed |
[73] S. J. Miller, S.-H. Kim, Z.-R. Chen, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 2108.
| Crossref | GoogleScholarGoogle Scholar |
[74] J. M. Chalker, C. S. C. Wood, B. G. Davis, J. Am. Chem. Soc. 2009, 131, 16346.
| Crossref | GoogleScholarGoogle Scholar | 19852502PubMed |
[75] J. R. O. Filho, W. C. Silva, J. C. M. Pereira, D. W. Franco, Inorg. Chim. Acta 2006, 359, 2888.
| Crossref | GoogleScholarGoogle Scholar |
[76] N. M. Giles, A. B. Watts, G. I. Giles, F. H. Fry, J. A. Littlechild, C. Jacob, Chem. Biol. 2003, 10, 677.
| Crossref | GoogleScholarGoogle Scholar | 12954327PubMed |
[77] J. M. Chalker, Aust. J. Chem. 2015, 68, 1801.
| Crossref | GoogleScholarGoogle Scholar |
[78] J. M. Chalker, Y. A. Lin, O. Boutureira, B. G. Davis, Chem. Commun. 2009, 3714.
| Crossref | GoogleScholarGoogle Scholar |
[79] Y. A. Lin, J. M. Chalker, B. G. Davis, ChemBioChem 2009, 10, 959.
| Crossref | GoogleScholarGoogle Scholar | 19343741PubMed |
[80] Y. A. Lin, J. M. Chalker, B. G. Davis, J. Am. Chem. Soc. 2010, 132, 16805.
| Crossref | GoogleScholarGoogle Scholar | 21050005PubMed |
[81] Y. A. Lin, J. M. Chalker, N. Floyd, G. J. L. Bernardes, B. G. Davis, J. Am. Chem. Soc. 2008, 130, 9642.
| Crossref | GoogleScholarGoogle Scholar | 18593118PubMed |
[82] G. A. Edwards, P. A. Culp, J. M. Chalker, Chem. Commun. 2015, 515.
| Crossref | GoogleScholarGoogle Scholar |
[83] H. Wang, H. Matsuhashi, B. D. Doan, S. N. Goodman, X. Ouyang, W. M. Clark, Tetrahedron 2009, 65, 6291.
| Crossref | GoogleScholarGoogle Scholar |
[84] S. H. Hong, D. P. Sanders, C. W. Lee, R. H. Grubbs, J. Am. Chem. Soc. 2005, 127, 17160.
| Crossref | GoogleScholarGoogle Scholar | 16332044PubMed |
[85] S. E. Clapham, A. Hadzovic, R. H. Morris, Coord. Chem. Rev. 2004, 248, 2201.
| Crossref | GoogleScholarGoogle Scholar |
[86] S. Krompiec, N. Kuźnik, M. Krompiec, R. Penczek, J. Mrzigod, A. Tórz, J. Mol. Catal. Chem. 2006, 253, 132.
| Crossref | GoogleScholarGoogle Scholar |
[87] B. Schmidt, Eur. J. Org. Chem. 2004, 1865.
| Crossref | GoogleScholarGoogle Scholar |
[88] G. C. Vougioukalakis, Chem. – Eur. J. 2012, 18, 8868.
| Crossref | GoogleScholarGoogle Scholar | 22689268PubMed |
[89] P. Wheeler, J. H. Phillips, R. L. Pederson, Org. Process Res. Dev. 2016, 20, 1182.
| Crossref | GoogleScholarGoogle Scholar |
[90] J. M. Phillips, M. Ahamed, X. Duan, R. N. Lamb, X. Qu, K. Zheng, J. Zou, J. M. Chalker, C. L. Raston, ACS Appl. Biol. Mater. 2019, 2, 488.
| Crossref | GoogleScholarGoogle Scholar |