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(01): 145-150
DOI: 10.1055/s-0036-1588589
DOI: 10.1055/s-0036-1588589
paper
Organocatalytic Alkyne Isomerizations under Flow Conditions Using Heterogeneous Bifunctional Polystyrene Bearing Phosphine and Phenol Groups
Further Information
Publication History
Received: 27 June 2016
Accepted after revision: 05 August 2016
Publication Date:
10 October 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201701/lookinside/thumbnails/ss-2016-z0440-op_10-1055_s-0036-1588589-1.jpg)
Abstract
A heterogeneous bifunctional polymer bearing phosphine and phenol groups was developed to catalyze the isomerization of electronically activated alkynes. This organocatalytic process provided the corresponding (E,E)-dienes and was shown to work under both batch and flow conditions.
Key words
rearrangement - organocatalysis - polymer-supported catalyst - phosphine - phenols - flow chemistrySupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588589.
- Supporting Information
-
References
- 1 Kwong CK.-W, Fu MY, Lam CS.-L, Toy PH. Synthesis 2008; 2307
- 2 For related DMAP-catalyzed alkyne isomerization reactions, see: Yue Y, Yu X.-Q, Pu L. Chem. Eur. J. 2009; 15: 5104
- 3 Trost BM, Kazmaier U. J. Am. Chem. Soc. 1992; 114: 7933
- 4 Guo C, Lu X. J. Chem. Soc., Perkin Trans. 1 1993; 1921
- 5 Rychnovsky SD, Kim J. J. Org. Chem. 1994; 59: 2659
- 6a Li M, O’Doherty GA. Org. Lett. 2006; 8: 3987
- 6b Li M, O’Doherty GA. Org. Lett. 2006; 8: 6087
- 6c Xing Y, O’Doherty GA. Org. Lett. 2009; 11: 1107
- 6d Wang Y, O’Doherty GA. J. Am. Chem. Soc. 2013; 135: 9334
- 6e Xia X, Toy PH. Synlett 2014; 25: 2787
- 7 Kwong CK.-W, Huang R, Zhang M, Shi M, Toy PH. Chem. Eur. J. 2007; 13: 2369
- 8 Kwong CK.-W, Fu MY, Law HC.-H, Toy PH. Synlett 2010; 2617
- 9a Leung PS.-W, Teng Y, Toy PH. Synlett 2010; 1997
- 9b Leung PS.-W, Teng Y, Toy PH. Org. Lett. 2010; 12: 4996
- 9c Teng Y, Lu J, Toy PH. Chem. Asian J. 2012; 7: 351
- 9d Xia X, Toy PH. Beilstein J. Org. Chem. 2014; 10: 1397
- 9e Hodges JC, Harikrishnan LS, Ault-Justus S. J. Comb. Chem. 2000; 2: 80
- 9f Toy PH, Janda K. Tetrahedron Lett. 1999; 40: 6329
- 10 Zhao L.-J, Kwong CK.-W, Shi M, Toy PH. Tetrahedron 2005; 61: 12026
- 11 Choi MK. W, He HS, Toy PH. J. Org. Chem. 2003; 68: 9831
- 12a Baxendale IR, Brocken L, Mallia CJ. Green Process. Synth. 2013; 2: 211
- 12b McQuade DT, Seeberger PH. J. Org. Chem. 2013; 78: 6384
- 12c Pastre JC, Browne DL, O’Brien M, Ley SV. Org. Process Res. Dev. 2013; 17: 1183
-
12d Wiles C, Watts P. Green Chem. 2012; 14: 38
- 12e Wegner J, Ceylan S, Kirschning A. Adv. Synth. Catal. 2012; 354: 17
-
12f Wegner J, Ceylan S, Kirschning A. Chem. Commun. 2011; 47: 4583
- 12g Jas G, Kirschning A. Chem. Eur. J. 2003; 9: 5708
- 13a Hartwig J, Kirschning A. Chem. Eur. J. 2016; 22: 3044
- 13b Hartwig J, Ceylan S, Kupracz L, Coutable L, Kirschning A. Angew. Chem. 2013; 125: 9995 ; Angew. Chem. Int. Ed., 2013, 52, 9813
- 13c Wegner J, Ceylan S, Friese C, Kirschning A. Eur. J. Org. Chem. 2010; 4372
- 13d Ceylan S, Klande T, Vogt C, Friese C, Kirschning A. Synlett 2010; 2009
- 13e Mennecke K, Kirschning A. Synthesis 2008; 3267
- 13f Baumann M, Baxendale IR, Ley SV, Nikbin N, Smith CD, Tierney JP. Org. Biomol. Chem. 2008; 6: 1577
- 13g Pericas MA, Herrerias CI, Sola L. Adv. Synth. Catal. 2008; 350: 927
- 13h Yamamoto H, Sasaki I, Hirai Y, Namba K, Imagawa H, Nishizawa M. Angew. Chem. Int. Ed. 2009; 48: 1244
- 13i Tagata T, Nishida M, Nishida A. Adv. Synth. Catal. 2010; 352: 1662
- 13j Shore G, Organ MG. Chem. Commun. 2008; 838
-
14a Ceylan S, Friese C, Lammel C, Mazac K, Kirschning A. Angew. Chem. Int. Ed. 2008; 47: 8950
- 14b Mennecke K, Cecilia R, Glasnov TN, Gruhl S, Vogt C, Feldhoff A, Larrubia Vargas MA, Kappe CO, Kunz U, Kirschning A. Adv. Synth. Catal. 2008; 350: 717
- 14c Kirschning A, Altwicker C, Dräger G, Harders J, Hoffmann N, Hoffmann U, Schönfeld H, Solodenko W, Kunz U. Angew. Chem. Int. Ed. 2001; 40: 3995
-
15 Michrowska A, Mennecke K, Kunz U, Kirschning A, Grela K. J. Am. Chem. Soc. 2006; 128: 13261
- 16a Matsumoto T, Ueno M, Wang N, Kobayashi S. Chem. Asian J. 2008; 3: 196
- 16b Nikbin N, Ladlow M, Ley SV. Org. Process Res. Dev. 2007; 11: 458
- 17 Bode JW, Carreira EM. J. Am. Chem. Soc. 2001; 123: 3611
For details regarding rasta resins, see:
For details regarding JandaJel, see:
Selected reviews on flow chemistry in organic synthesis: