Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2017; 49(17): 3945-3951
DOI: 10.1055/s-0036-1588813
DOI: 10.1055/s-0036-1588813
special topic
Ethylene Glycol Assisted Intermolecular Pauson–Khand Reaction
Supported by: We thank the Spanish Ministerio de Economia y Competividad (CTQ2014-56361-P) and IRB Barcelona for financial support. IRB Barcelona is the recipient of a Severo Ochoa Award of Excellence from MINECO (Government of Spain). CTQ2014-56361-PFurther Information
Publication History
Received: 15 March 2017
Accepted after revision: 10 April 2017
Publication Date:
27 April 2017 (online)
![](https://www.thieme-connect.de/media/synthesis/201717/lookinside/thumbnails/ss-2017-c0165-st_10-1055_s-0036-1588813-1.jpg)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588813. Included are experimental procedures for the preparation of alkynes and alkynehexacarbonyldicobalt complexes, as well as 1H and 13C spectra of the new PK adducts synthesized in this work.
- Supporting Information
-
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
- 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
- 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
- 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
Other Pauson–Khand reactions with ethylene:
For other additives tried in the intermolecular PKR, see:
This system is typically accessed by indirect routes involving ring expansion reactions: