Heck couplings at room temperature in nanometer aqueous micelles

Organic Letters

Volumn 10, Issue 7, 2008, Pages 1329-1332

  Lipshutz, Bruce H ^a   Taft, Benjamin R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 48949099423     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702755g     Document Type: Article

References (44)

1. (a) Li, C.-J.; Chen, L. Chem. Soc. Rev. 2006, 35, 68.
2. (b) Shaughnessy, K. H. Eur. J. Org. Chem. 2006, 1827.
3. (c) Li, C.-J. Chem. Rev. 2005, 105, 3095.
4. (d) Shaughnessy, K. H.; DeVasher, R. B. Curr. Org. Chem. 2005, 9, 585.
5. (e) Aqueous-Phase Organometallic Catalysis, 2nd ed.; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
6. Oehme, G.; Paetzold, E.; Dwars, T. Angew. Chem., Int. Ed. 2005, 44, 7174.
7. (a) Whiting, A.; Knowles, J. P. Org. Biomol. Chem. 2007, 5, 31.
8. (b) Jones, W. C.; Sluys, M.; Phan, N. Adv. Synth. Catal. 2006, 348, 609.
9. (c) Yus, M.; Beletskaya, I. P.; Alonso, F. Tetrahedron 2005, 61, 11771.
10. (d) Beletskaya, I. P.; Cheprakov, A. V. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, NY, 2002; Vol. 2, pp. 2957-3006.
11. (e) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
12. (a) Alacid, E.; Najera, C. Synlett 2006, 2959.
13. (b) Schonfelder, D.; Nuyken, O.; Weberskirch, R. J. Organomet. Chem. 2005, 690, 4648.
14. (c) Schonfelder, D.; Fischer, K.; Schmidt, M.; Nuyken, O.; Weberskirch, R. Macromolecules 2005, 38, 254.
15. Sigma-Aldrich catalog #'s (a) 234729, (b) P4391, (c) L3771.
16. PCI-102B Eastman Vitamin E TPGS NF - Applications and Properties. http://www.eastman.com/NR/rdonlyres/A2FE037B-0778-4A90-A0FC-5D07BE51064A/0/ PCI102.pdf (accessed August 2007).
17. (a) Borowy-Borowski, H.; Sikorska-Walker, M.; Walker, P. R. Water-Soluble Compositions of Bioactive Lipophilic Compounds. U.S. Patent 6,-045,826, Apr 4, 2000.
18. (b) Borowy-Borowski, H.; Sikorska-Walker, M.; Walker, P. R. Water-Soluble Compositions of Bioactive Lipophilic Compounds. U.S. Patent 6,191,172, Feb 20, 2001.
19. (c) Borowy-Borowski, H.; Sikorska-Walker, M.; Walker, P. R. Water-Soluble Compositions of Bioactive Lipophilic Compounds. U.S. Patent 6,632,443, Oct 14, 2003.
20. (a) Blackmond, D. G.; Armstrong, A.; Coombe, V.; Wells, A. Angew. Chem., Int. Ed. 2007, 46, 3798.
21. Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolib, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275.
22. (a) Li, J.-H.; Hu, X.-C.; Liang, Y.; Xie, Y.-X. Tetrahedron 2006, 62, 31.
23. (b) Najera, C.; Botella, L. J. Org. Chem. 2005, 70, 4360.
24. (c) Shaughnessy, K. H.; Moore, L. R.; DeVasher, R. B. J. Org. Chem. 2004, 69, 7919.
25. (d) Hartwig, J. F.; Shaughnessy, K. H.; Stauffer, S. R.; Stambuli, J. P. J. Am. Chem. Soc. 2001, 123, 2677.
26. (a) Organic Reactions in Water; Lindstrom, U. M., Ed.; Blackwell Publishing Ltd.: Oxford, UK, 2007.
27. (b) Klijn, J. E.; Engberts, J. B. Nature 2005, 435, 746.
28. 2 (CAS no. 95408-45-0) was generously supplied by Dr. Thomas J. Colacot (E-mail: colactj@jmusa.com, Johnson-Matthey).
29. The critical micelle concentration for PTS in water has been determined to be 0.281 mg/g at room temperature.
30. A more detailed study will be reported shortly.
31. 2 (CAS no. 172418-32-5) was used instead of 7, improving selectivity (GC yield 89 vs 71%).
32. Vazquez, E.; Caron, S.; Stevens, R.; Nakao, K.; Koike, H.; Yoshinori, M. J. Org. Chem. 2003, 68, 4104.
33. 1-Octyl-4-vinyl-1,2,3-triazole (12) was prepared via copper(I)-catalyzed "click" cycloaddition of octyl-azide with but-3-ynyl methanesulfonate followed by sodium iodide promoted elimination.
34. Lipshutz, B. H.; Petersen, T. B. Unpublished work.
35. Borkovec, M. Measuring particle size by light scattering. Handbook of Applied Surface and Colloid Chemistry; John Wiley & Sons Ltd.: Chichester, UK, 2002; pp 357-370.
36. Kaler, E. W.; Gonzalez, Y. Curr. Opin. Colloid Interface Sci. 2005, 10, 256.
37. (a) Cai, C.; Jiang, J.-Z. J. Colloid Interface Sci. 2006, 299, 938.
38. (b) Zhou, M.-M.; Wang, Z.; Zhou, Y.; Pan, C.; Gan, C.; Zha, Z.; Zhang, Z. J. Org. Chem. 2006, 71, 4339.
39. (c) Moeller, K. D.; Tian, J. Org. Lett. 2005, 7, 5381.
40. (d) Handy, S. T.; Okello, M. Tetrahedron Lett. 2003, 44, 8395.
41. (e) Genet, J.-P.; Savignac, M.; Michelet, V.; Genin, E.; Amengual, R. Adv. Synth. Catal. 2002, 344, 393.
42. Available from Sigma-Aldrich in May, 2008, as an aqueous solution (catalog #698717).
43. 2, 13.0 mg, 0.02 mmol) and 4-iodoanisole (234 mg, 1.0 mmol) were added under argon to a 5.0 mL microwave vial equipped with a large stir bar and Teflon lined septum. PTS solution (2.0 mL, 15 wt%), triethylamine (416 μL, 3.0 mmol), and t-butyl acrylate (290 μL, 2.0 mmol) were added by syringe. The heterogeneous mixture was stirred vigorously at rt, becoming pseudo-homogeneous after 20-40 min. Reaction progress was monitored by TLC (1: 10, EtOAc/hexanes). Upon consumption of aryl iodide (∼5 h), the dark brown mixture was diluted with EtOAc (2.0 mL) and filtered through a pad of silica gel using EtOAc (15 mL) as eluent. The volatiles were removed on a rotary evaporator and the crude product was purified by silica gel chromatography (1:10, EtOAc/hexanes) to yield 215 mg (92%) of a light tan solid. Spectral data matched that reported in the literature.
44. (b) Tang, Y.; Yu, Y.; Xia, W.; Song, Y. Huang, Z. J. Org. Chem. 2002, 67, 3096-3103.