Synthesis, Table of Contents Synthesis 2017; 49(17): 3945-3951DOI: 10.1055/s-0036-1588813 special topic © Georg Thieme Verlag Stuttgart · New YorkEthylene Glycol Assisted Intermolecular Pauson–Khand Reaction Authors Author Affiliations Albert Cabré a Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Baldiri Reixac 10, Barcelona 08028, Spain Email: antoni.riera@irbbarcelona.org Email: xavier.verdaguer@irbbarcelona.org Xavier Verdaguer * a Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Baldiri Reixac 10, Barcelona 08028, Spain Email: antoni.riera@irbbarcelona.org Email: xavier.verdaguer@irbbarcelona.org b Departament de Química Inorgànica i Orgànica, Secció Orgànica, Universitat de Barcelona, Martí i Franquès 1, Barcelona 08028, Spain Antoni Riera * a Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Baldiri Reixac 10, Barcelona 08028, Spain Email: antoni.riera@irbbarcelona.org Email: xavier.verdaguer@irbbarcelona.org b Departament de Química Inorgànica i Orgànica, Secció Orgànica, Universitat de Barcelona, Martí i Franquès 1, Barcelona 08028, Spain Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Published as part of the Special Topic Cobalt in Organic Synthesis Abstract The use of ethylene glycol as additive in the N-oxide-promoted intermolecular Pauson–Khand reaction (PKR) has been studied. The addition of 15% ethylene glycol to the reaction mixture consistently increased (from 20% up to 2–4-fold) the reaction yields. Key words Key wordsPauson–Khand reaction - cobalt - ethylene glycol - cyclopentenones - cycloaddition Full Text References References 1a Omae I. Appl. Organomet. Chem. 2007; 21: 318 1b Strübing D. Beller M. In Catalytic Carbonylation Reactions . Beller M. Springer; Berlin: 2006: 165 1c Pérez-Castells J. In Metal Catalyzed Cascade Reactions . Müller TJ. J. Springer; Berlin: 2006: 207 1d Laschat S. Becheanu A. Bell T. Baro A. Synlett 2005; 2547 1e Boñaga LV. R. Krafft ME. Tetrahedron 2004; 60: 9795 1f Rodríguez Rivero M. Adrio J. Carretero JC. Eur. J. Org. Chem. 2002; 2881 1g Brummond KM. Kent JL. Tetrahedron 2000; 56: 3263 1h Fletcher AJ. Christie SD. R. J. Chem. Soc., Perkin Trans. 1 2000; 1657 2a Chuang KV. Xu C. Reisman SE. Science 2016; 353: 912 2b Verdaguer X. Science 2016; 353: 866 2c Gibson SE. Mainolfi N. Angew. Chem. Int. Ed. 2005; 44: 3022 3 Marchueta I. Verdaguer X. Moyano A. Pericàs MA. Riera A. Org. Lett. 2001; 3: 3193 Other Pauson–Khand reactions with ethylene: 4a Donker-Voort JG. Gordon AR. Johnstone WC. Kerr J. Lange U. Tetrahedron 1996; 52: 7391 4b Gordon AR. Johnstone CW. Kerr J. Synlett 1995; 1083 4c Rautenstrauch V. Megard P. Conesa J. Kuester W. Angew. Chem., Int. Ed. Engl. 1990; 29: 1413 5a The Pauson-Khand Reaction: Scope, Variations and Applications. Ríos Torres R. Wiley; Chichester: 2012 5b Lee H.-W. Kwong F.-Y. Eur. J. Org. Chem. 2010; 789 5c Blanco-Urgoiti J. Anorbe L. Perez-Serrano L. Dominguez G. Perez-Castells J. Chem. Soc. Rev. 2004; 33: 32 For other additives tried in the intermolecular PKR, see: 6a Wang Y. Xu L. Yu R. Chen J. Yang Z. Chem. Commun. 2012; 48: 8183 6b Gibson SE. Johnstone C. Stevenazzi A. Tetrahedron 2002; 58: 4937 6c Hayashi M. Hashimoto Y. Yamamoto Y. Usuki J. Saigo K. Angew. Chem. Int. Ed. 2000; 39: 631 6d Sugihara T. Yamaguchi M. Synlett 1998; 1384 6e Jeong N. Hwang SH. Lee Y. Chung YK. J. Am. Chem. Soc. 1994; 116: 3159 7a Kerr WJ. McLaughlin MJ. Pauson PL. Robertson SM. J. Organomet. Chem. 2001; 630: 104 7b Jeong N. Chung YK. Lee BY. Lee SH. Yoo S.-E. Synlett 1991; 204 8 Shambayani S. Crowe WE. Schreiber SL. Tetrahedron Lett. 1990; 31: 5289 9 Hay AM. Kerr WJ. Kirk GG. Middlemiss D. Organometallics 1995; 14: 4986 10 Su S. Rodriguez RA. Baran PS. J. Am. Chem. Soc. 2011; 133: 13922 11 For other examples of MEG as cobalt NPs stabilizer, see: Muller J.-L. Klankermayer J. Leitner W. Chem. Commun. 2007; 1939 12a Ford JG. Kerr WJ. Kirk GG. Lindsay DM. Middlemiss D. Synlett 2000; 1415 12b Kerr WJ. Lindsay DM. Watson SP. Chem. Commun. 1999; 2551 13a Kerr WJ. McLaughlin M. Pauson PL. Robertson SM. J. Organomet. Chem. 2001; 630: 104 13b Kerr WJ. McLaughlin M. Pauson PL. Robertson SM. Chem. Commun. 1999; 2171 14 Lledo A. Fuster A. Reves M. Verdaguer X. Riera A. Chem. Commun. 2013; 49: 3055 This system is typically accessed by indirect routes involving ring expansion reactions: 15a Fan X. Zhuo L.-G. Tu YQ. Yu Z.-X. Tetrahedron 2009; 65: 4709 15b Shinohara I. Nagaoka H. Tetrahedron Lett. 2004; 45: 1495 15c Roxburgh CJ. Tetrahedron 1993; 49: 10749 16a Vázquez-Romero A. Verdaguer X. Riera A. Eur. J. Org. Chem. 2013; 1716 16b Vázquez-Romero A. Cárdenas L. Blasi E. Verdaguer X. Riera A. Org. Lett. 2009; 11: 3104 17a Jahn U. Galano J.-M. Durand T. Angew. Chem. Int. Ed. 2008; 47: 5894 17b Das UN. Biotechnol. J. 2006; 1: 420 17c Marks F. Fürstenberger G. Prostaglandins, Leukotrienes and other Eicosanoids . Wiley-VCH; Weinheim: 1999 17d Rokach J. Khanapure SP. Hwang S.-W. Adiyaman M. Lawson JA. FitzGerald GA. Prostaglandins 1997; 54: 823 18a Blanco-Urgoiti J. Casarrubios L. Domínguez G. Pérez-Castells J. Tetrahedron Lett. 2002; 43: 5763 18b Pérez-Serrano L. Casarrubios L. Domínguez G. Pérez-Castells J. Org. Lett. 1999; 1: 1187 19 Rausch BJ. Becker H. Gleiter R. Rominger F. Synlett 2002; 723 20 Jeong N. Hwang SH. Angew. Chem. Int. Ed. 2000; 39: 636 21 Fager-Jokela E. Muuronen M. Khaizourane H. Vázquez-Romero A. Verdaguer X. Riera A. Helaja J. J. Org. Chem. 2014; 79: 10999 22a Aiguabella N. Pesquer A. Verdaguer X. Riera A. Org. Lett. 2013; 15: 2696 22b Vázquez-Romero A. Rodríguez J. Lledó A. Verdaguer X. Riera A. Org. Lett. 2008; 10: 4509 22c Shih C. Fritzen EL. Swenton JS. J. Org. Chem. 1980; 45: 4462 23 Iqbal M. Li Y. Evans P. Tetrahedron 2004; 60: 2531 24 Bonazzi S. Binaghi M. Fellay C. Wach J.-Y. Gademann K. Synthesis 2010; 631 Supplementary Material Supplementary Material Supporting Information (PDF)