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Synthesis 2018; 50(08): 1711-1720
DOI: 10.1055/s-0036-1591878
DOI: 10.1055/s-0036-1591878
paper
Synthesis of Non-Conjugated Trienes via In Situ Hydrovinylation/Wittig Olefination of Unsaturated Phosphonium Salts
Further Information
Publication History
Received: 30 November 2017
Accepted: 04 December 2017
Publication Date:
22 December 2017 (online)
![](https://www.thieme-connect.de/media/synthesis/201808/lookinside/thumbnails/ss-2017-z0771-op_10-1055_s-0036-1591878-1.jpg)
Dedicated to Prof. Hans-Jürgen Schäfer on the occasion of his 80th birthday.
Abstract
A cobalt-catalysed 1,4-hydrovinylation reaction is successfully applied in a sequential three-component transformation of unsaturated phosphonium bromides, 1,3-dienes, and aldehydes leading to non-conjugated products with a 1,4-diene subunit in good to excellent yields. The hydrovinylation provides regioselectively diene structures with one exo double bond whereas the third double bond can be introduced via an in situ Wittig or Horner–Wadsworth–Emmons olefination leading to 1,4,7-trienes suitable for further double bond functionalisations.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591878.
- Supporting Information
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References
- 1a Hilt G. du Mesnil F.-X. Lüers S. Angew. Chem. Int. Ed. 2001; 40: 387
- 1b Hilt G. Lüers S. Synthesis 2002; 609
- 1c Hilt G. Treutwein J. Chem. Commun. 2009; 1395
- 1d Hilt G. Eur. J. Org. Chem. 2012; 4441
- 1e Röse P. Emge S. Yoshida J. Hilt G. Beilstein J. Org. Chem. 2015; 11: 174
- 2a Sharma RK. RajanBabu TV. J. Am. Chem. Soc. 2010; 132: 3295
- 2b Biswas S. Page JP. Dewese KR. RajanBabu TV. J. Am. Chem. Soc. 2015; 137: 14268
- 2c Timsina YN. Sharma RK. RajanBabu TV. Chem. Sci. 2015; 6: 3994
- 2d Vogt D. Angew. Chem. Int. Ed. 2010; 49: 7166
- 2e Page JP. RajanBabu TV. J. Am. Chem. Soc. 2012; 134: 6556
- 2f Hilt G. ChemCatChem 2015; 7: 1639
- 2g Jing SM. Balasanthiran V. Pagar V. Gallucci JC. RajanBabu TV. J. Am. Chem. Soc. 2017; DOI: 10.1021/jacs.7b10055
- 3a Arndt M. Dindaroğlu M. Schmalz H.-G. Hilt G. Synthesis 2012; 44: 3534
- 3b Hilt G. Roesner S. Synthesis 2011; 662
- 3c Grutters MM. P. Müller C. Vogt D. J. Am. Chem. Soc. 2006; 128: 7414
- 3d Arndt M. Dindaroğlu M. Schmalz H.-G. Hilt G. Org. Lett. 2011; 13: 6236
- 3e Hilt G. Danz M. Treutwein J. Org. Lett. 2009; 11: 3322
- 3f Grutters MM. P. van der Vlugt JI. Pei X. Mills AM. Lutz M. Spek AL. Müller C. Moberg C. Vogt D. Adv. Synth. Catal. 2009; 351: 2199
- 4a Erver F. Hilt G. Org. Lett. 2012; 14: 1884
- 4b Erver F. Kuttner JR. Hilt G. J. Org. Chem. 2012; 77: 8375
- 4c Timsina YN. Biswas S. RajanBabu TV. J. Am. Chem. Soc. 2014; 136: 6215
- 5a Hilt G. Arndt M. Weske DF. Synthesis 2010; 1321
- 5b Arndt M. Reinhold A. Hilt G. J. Org. Chem. 2010; 75: 5203
- 5c Kersten L. Hilt G. Adv. Synth. Catal. 2012; 354: 863
- 5d Kersten L. Harms K. Hilt G. J. Org. Chem. 2014; 79: 11661
- 6 For the combination of the Wittig reaction with an ene-reaction, see: Majik MS. Parameswaran PS. Tilve SG. J. Org. Chem. 2009; 74: 3591
- 7a Dörfler J. Preuß T. Schischko A. Schmidtmann M. Doye S. Angew. Chem. Int. Ed. 2014; 53: 7918
- 7b Kanno O. Kuriyama W. Wang ZJ. Toste FD. Angew. Chem. Int. Ed. 2011; 50: 9919
- 7c Brouwer C. He C. Angew. Chem. Int. Ed. 2006; 45: 1744
- 7d Dörfler J. Bytyqi B. Hüller S. Mann NM. Brahms C. Schmidtmann M. Doye S. Adv. Synth. Catal. 2015; 357: 2265
- 7e Perrier A. Ferreira M. Reek JN. H. van der Vlugt JI. Catal. Sci. Technol. 2013; 3: 1375
- 7f Han X. Widenhoefer RA. Angew. Chem. Int. Ed. 2006; 45: 1747
- 7g Pawlas J. Nakao Y. Kawatsura M. Hartwig JF. J. Am. Chem. Soc. 2002; 124: 3669
- 7h Thullen SM. Rovis T. J. Am. Chem. Soc. 2017; 139: 15504
- 7i Rousseau G. Lebeuf R. Schenk K. Castet F. Robert F. Landais Y. Chem. Eur. J. 2014; 20: 14771
- 9 dppe = 1,2-bis(diphenylphosphino)ethane.
- 10 Weber F. Schmidt A. Röse P. Fischer M. Burghaus O. Hilt G. Org. Lett. 2015; 17: 2952
For a selection of enantioselective hydrovinylation reactions, see:
For a selection of regioselective hydrovinylations, see:
For multiple cobalt catalysis, see:
For the synthesis of homoallylic alcohols and polycarbonyl compounds, see: