[en] A continuous-flow Pd-catalyzed oxidative carbonylation protocol utilizing CO and O2 gas for the synthesis of carbonylated heterocycles is described. The optimization of temperature, pressure, CO/O2 ratio, catalyst loading, and reaction time resulted in process intensified conditions for this transformation. The optimized continuous flow conditions (120 °C, 20 bar pressure, 24 min residence time) were used to prepare a number of benzoxazolone, 2-benzoxazolidinone, and other biologically and synthetically important five- and six-membered carbonylated heterocycles in good overall yield and purity (14 examples). The continuous-flow process enables the safe and scalable oxidative carbonylation using CO/O2 under elevated pressures and temperatures.
Disciplines :
Chemistry
Author, co-author :
Chen, Yuesu ; Université de Liège - ULiège > Molecular Systems (MolSys) ; Institute of Chemistry, University of Graz, NAWI Graz, Graz, Austria
Hone, Christopher A.; Institute of Chemistry, University of Graz, NAWI Graz, Graz, Austria ; Research Center Pharmaceutical Engineering GmbH (RCPE), Graz, Austria
Gutmann, Bernhard; Institute of Chemistry, University of Graz, NAWI Graz, Graz, Austria ; Research Center Pharmaceutical Engineering GmbH (RCPE), Graz, Austria
Kappe, C. Oliver ; Institute of Chemistry, University of Graz, NAWI Graz, Graz, Austria ; Research Center Pharmaceutical Engineering GmbH (RCPE), Graz, Austria
Language :
English
Title :
Continuous Flow Synthesis of Carbonylated Heterocycles via Pd-Catalyzed Oxidative Carbonylation Using CO and O2 at Elevated Temperatures and Pressures
Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press Ltd.: San Diego, 1985.
Barnard, C. F. J. Organometallics 2008, 27, 5402 10.1021/om800549q
Bai, Y.; Davis, D. C.; Dai, M. J. Org. Chem. 2017, 82, 2319 10.1021/acs.joc.7b00009
Reddy, K. I.; Aruna, C.; Babu, S. K.; Vijayakumar, V.; Manisha, M.; Sridevi, J. P.; Yogeeswari, P.; Sriram, D. RSC Adv. 2014, 4, 59594 10.1039/C4RA07123A
Ucar, H.; Van derpoorten, K.; Cacciaguerra, S.; Spampinato, S.; Stables, J. P.; Depovere, P.; Isa, M.; Masereel, B.; Delarge, J.; Poupaert, J. H. J. Med. Chem. 1998, 41, 3102 10.1021/jm980259g
Ucar, H.; Van derpoorten, K.; Cacciaguerra, S.; Spampinato, S.; Stables, J. P.; Depovere, P.; Isa, M.; Masereel, B.; Delarge, J.; Poupaert, J. H. J. Med. Chem. 1998, 41, 1138 10.1021/jm970682+
Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127 10.1021/ja00398a058
Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737 10.1021/ja00370a050
Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1984, 106, 4261 10.1021/ja00327a031
Ceccarelli, S. M.; Jaeschke, G.; Buettelmann, B.; Huwyler, J.; Kolczewski, S.; Peters, J.-U.; Prinssen, E.; Porter, R.; Spooren, W.; Vieira, E. Bioorg. Med. Chem. Lett. 2007, 17, 1302 10.1016/j.bmcl.2006.12.006
Vo, L.; Ciula, J.; Gooding, O. W. Org. Process Res. Dev. 2003, 7, 514 10.1021/op034033l
Musser, J. H.; Jones, H.; Sciortino, S.; Bailey, K.; Coutts, S. M.; Khandwala, A.; Sonnino-Goldman, P.; Leibowitz, M.; Wolf, P.; Neiss, E. S. J. Med. Chem. 1985, 28, 1255 10.1021/jm00147a023
Hanslick, R. S.; Bruce, W. F.; Mascitti, A. Org. Synth. 1953, 33, 74 10.15227/orgsyn.033.0074
Close, W. J.; Tiffany, B. D.; Spielman, M. A. J. Am. Chem. Soc. 1949, 71, 1265 10.1021/ja01172a036
Guidi, S.; Calmanti, R.; Noè, M.; Perosa, A.; Selva, M. ACS Sustainable Chem. Eng. 2016, 4, 6144 10.1021/acssuschemeng.6b01633
Pulla, S.; Unnikrishnan, V.; Ramidi, P.; Sullivan, S. Z.; Ghosh, A.; Dallas, J. L.; Munshi, P. J. Mol. Catal. A: Chem. 2011, 338, 33 10.1016/j.molcata.2011.01.022
Kim, S.; Ko, Y. K. Heterocycles 1986, 24, 1625 10.3987/R-1986-06-1625
PeCa-Lýpez, M.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2016, 55, 7826 10.1002/anie.201600698
Bala, M.; Verma, P. K.; Sharma, D.; Kumar, N.; Singh, B. Mol. Diversity 2015, 19, 263 10.1007/s11030-015-9572-8
Bhanage, B. M.; Fujita, S.-i.; Ikushima, Y.; Arai, M. Green Chem. 2004, 6, 78 10.1039/b310115k
Mancuso, R.; Raut, D. S.; Della Ca, N. D.; Fini, F.; Carfagna, C.; Gabriele, B. ChemSusChem 2015, 8, 2204 10.1002/cssc.201500343
Peng, X.; Li, F.; Hu, X.; Xia, C.; Sandoval, C. A. Chin. J. Catal. 2008, 29, 638 10.1016/S1872-2067(08)60062-5
Li, F.; Xia, C. Tetrahedron Lett. 2007, 48, 4845 10.1016/j.tetlet.2007.05.048
Li, F.; Peng, X.; Xia, C.; Hu, B. Chin. J. Chem. 2005, 23, 643 10.1002/cjoc.200590643
Gabriele, B.; Mancuso, R.; Salerno, G.; Costa, M. J. Org. Chem. 2003, 68, 601 10.1021/jo026532a
Gabriele, B.; Salerno, G.; Brindisi, D.; Costa, M.; Chiusoli, G. P. Org. Lett. 2000, 2, 625 10.1021/ol9913789
Li, F.-W.; Xia, C.-G. J. Catal. 2004, 227, 542 10.1016/j.jcat.2004.07.019
Giannoccaro, P.; Ferragina, C.; Gargano, M.; Quaranta, E. Appl. Catal., A 2010, 375, 78 10.1016/j.apcata.2009.12.022
Mallia, C. J.; Baxendale, I. R. Org. Process Res. Dev. 2016, 20, 327 10.1021/acs.oprd.5b00222
Hone, C. A.; Roberge, D.; Kappe, C. O. ChemSusChem 2017, 10, 32 10.1002/cssc.201601321
Pieber, B.; Kappe, C. O. Top. Organomet. Chem. 2015, 57, 97 10.1007/3418-2015-133
Pieber, B.; Kappe, C. O. Chim. Oggi/Chem. Today 2016, 34, 38
A review on the safety accessment of flow process: Kockmann, N.; Thenée, P.; Fleischer-Trebes, C.; Laudadio, G.; Noël, T. React. Chem. Eng. 2017, 2, 258 10.1039/C7RE00021A
Gutmann, B.; Cantillo, D.; Weigl, U.; Cox, D. P.; Kappe, C. O. Eur. J. Org. Chem. 2017, 2017, 914 10.1002/ejoc.201601453
Gutmann, B.; Elsner, P.; Cox, D. P.; Weigl, U.; Roberge, D. M.; Kappe, C. O. ACS Sustainable Chem. Eng. 2016, 4, 6048 10.1021/acssuschemeng.6b01371
Gutmann, B.; Weigl, U.; Cox, D. P.; Kappe, C. O. Chem.-Eur. J. 2016, 22, 10393 10.1002/chem.201601902
Pieber, B.; Cox, D. P.; Kappe, C. O. Org. Process Res. Dev. 2016, 20, 376 10.1021/acs.oprd.5b00370
Hone, C.; O'Kearney-McMullan, A.; Munday, R.; Kappe, C. O. ChemCatChem. 2017, 9, 10.1002/cctc.201700671.
Erdmann, N.; Su, Y.; Bosmans, B.; Hessel, V.; Noël, T. Org. Process Res. Dev. 2016, 20, 831 10.1021/acs.oprd.6b00044
Glotz, G.; Gutmann, B.; Hanselmann, P.; Kulesza, A.; Roberge, D.; Kappe, C. O. RSC Adv. 2017, 7, 10469 10.1039/C7RA01087G
Alonso, N.; Munoz, J.; de, M.; Egle, B.; Vrijdag, J. L.; De Borggraeve, W. M.; de la Hoz, A.; Diaz-Ortiz, A.; Alcazar, J. J. Flow Chem. 2014, 4, 105 10.1556/JFC-D-14-00005
Kelly, C. B.; Lee, C.; Mercadante, M. A.; Leadbeater, N. E. Org. Process Res. Dev. 2011, 15, 717 10.1021/op200037n
Fukuyama, T.; Totoki, T.; Ryu, I. Org. Lett. 2014, 16, 5632 10.1021/ol5026958
Gong, X.; Miller, P. W.; Gee, A. D.; Long, N. J.; de Mello, A. J.; Vilar, R. Chem.-Eur. J. 2012, 18, 2768 10.1002/chem.201104059
Miller, P. W.; Jennings, L. E.; de Mello, A. J.; Gee, A. D.; Long, N. J.; Vilar, R. Adv. Synth. Catal. 2009, 351, 3260 10.1002/adsc.200900563
Miller, P. W.; Long, N. J.; de Mello, A. J.; Vilar, R.; Audrain, H.; Bender, D.; Passchier, J.; Gee, A. Angew. Chem., Int. Ed. 2007, 46, 2875 10.1002/anie.200604541
Rahman, Md. T.; Fukuyama, T.; Kamata, N.; Sato, M.; Ryu, I. Chem. Commun. 2006, 2236 10.1039/b600970k
Miller, P. W.; Long, N. J.; de Mello, A. J.; Vilar, R.; Passchier, J.; Gee, A. Chem. Commun. 2006, 546 10.1039/B515710B
Gong, X.; Miller, P. W.; Gee, A. D.; Long, N. J.; de Mello, A. J.; Vilar, R. Chem.-Eur. J. 2012, 18, 2768 10.1002/chem.201104059
Hansen, S. V. F.; Wilson, Z. E.; Ulven, T.; Ley, S. V. React. Chem.Eng. 2016, 1, 280 10.1039/C6RE00020G
Mallia, C. J.; Walter, G. C.; Baxendale, I. R. Beilstein J. Org. Chem. 2016, 12, 1503 10.3762/bjoc.12.147
Gross, U.; Koos, P.; O'Brien, M.; Polyzos, A.; Ley, S. V. Eur. J. Org. Chem. 2014, 2014, 6418 10.1002/ejoc.201402804
Brancour, C.; Fukuyama, T.; Mukai, Y.; Skrydstrup, T.; Ryu, I. Org. Lett. 2013, 15, 2794 10.1021/ol401092a
Mercadante, M. A.; Leadbeater, N. E. Org. Biomol. Chem. 2011, 9, 6575 10.1039/c1ob05808h
Fukuyama, T.; Mukai, Y.; Ryu, I. Beilstein J. Org. Chem. 2011, 7, 1288 10.3762/bjoc.7.149
For a review on the synthesis of dialkyl carbonates, see: Huang, S.; Yan, B.; Wang, S.; Ma, X. Chem. Soc. Rev. 2015, 44, 3079 10.1039/C4CS00374H
Zheng, H.-Y.; Wang, J.-Z.; Li, Z.; Yan, L.-F.; Wen, J. Z. Fuel Process. Technol. 2016, 152, 367 10.1016/j.fuproc.2016.06.036
Han, M. S.; Lee, B. G.; Ahn, B. S.; Kim, H. S.; Moon, D. J.; Hong, S. I. J. Mol. Catal. A: Chem. 2003, 203, 137 10.1016/S1381-1169(03)00131-6
Han, M. S.; Lee, B. G.; Suh, I.; Kim, H. S.; Ahn, B. S.; Hong, S. I. J. Mol. Catal. A: Chem. 2001, 170, 225 10.1016/S1381-1169(01)00073-5
Watt, G. W.; Knifton, J. F. Inorg. Chem. 1968, 7, 1443 10.1021/ic50065a037
Tanaka, K.; Tasaka, M.; Cao, H.; Shionoya, M. Supramol. Chem. 2002, 14, 255 10.1080/10610270290026167
Gutmann, B.; Glasnov, T. N.; Razzaq, T.; Goessler, W.; Roberge, D. M.; Kappe, C. O. Beilstein J. Org. Chem. 2011, 7, 503 10.3762/bjoc.7.59
Shore, G.; Morin, S.; Organ, M. G. Angew. Chem., Int. Ed. 2006, 45, 2761 10.1002/anie.200503600
Shore, G.; Yoo, W. J.; Li, C. J.; Organ, M. G. Chem.-Eur. J. 2010, 16, 126 10.1002/chem.200902396
Reetz, M. T.; de Vries, J. G. Chem. Commun. 2004, 1559 10.1039/b406719n
Phan, N. T. S.; Van der Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609 10.1002/adsc.200505473
de Vries, A. H. M.; Parlevliet, F. J.; Schmieder-van de Vondervoort, L.; Mommers, J. H. M.; Henderickx, H. J. W.; Walet, M. A. M.; de Vries, J. G. Adv. Synth. Catal. 2002, 344, 996 10.1002/1615-4169(200210)344:9<996::AID-ADSC996>3.0.CO;2-J
Jawale, D. V.; Gravel, E.; Geertsen, V.; Li, H.; Shah, N.; Namboothiri, I. N. N.; Doris, E. ChemCatChem 2014, 6, 719 10.1002/cctc.201301069
Boyce, G. R.; Johnson, J. S. J. Org. Chem. 2016, 81, 1712 10.1021/acs.joc.5b02693
Xu, Y.-S.; Tang, Y.; Feng, H.-J.; Liu, J.-T.; Hsung, R. P. Org. Lett. 2015, 17, 572 10.1021/ol503591d
Miyake, G. M.; DiRocco, D. A.; Liu, Q.; Oberg, K. M.; Bayram, E.; Finke, R. G.; Rovis, T.; Chen, E. Y.-X. Macromolecules 2010, 43, 7504 10.1021/ma101310n
Nickerson, L. A.; Huynh, V.; Balmond, E. I.; Cramer, S. P.; Shaw, J. T. J. Org. Chem. 2016, 81, 11404 10.1021/acs.joc.6b01997
Balasubramanian, N.; Mandal, T.; Cook, G. R. Org. Lett. 2015, 17, 314 10.1021/ol5034207
McKennon, M. J.; Meyers, A. I.; Drauz, K.; Schwarm, M. J. Org. Chem. 1993, 58, 3568 10.1021/jo00065a020
Atkinson, R. S.; Judkins, B. D. J. Chem. Soc., Perkin Trans. 2 1981, 2, 509 10.1039/p29810000509
