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Organic Letters

Volumn 10, Issue 7, 2008, Pages 1325-1328

Olefin cross-metathesis reactions at room temperature using the nonionic amphiphile "PTS": Just add water

(4) Lipshutz, Bruce H a Aguinaldo, Grant T a Ghorai, Subir a Voigtritter, Karl a

a UNIVERSITY OF CALIFORNIA (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 44949187649 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol800028x Document Type: Article

Times cited : (163)

References (56)

1
- 59849104613
- Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie: London, 1998.
- (a) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie: London, 1998.

2
- 0036703508
- (b) Lindstrom, U. M. Chem. Rev. 2002, 102, 2751-2772.
- (2002) Chem. Rev , vol.102 , pp. 2751-2772
- Lindstrom, U.M.¹

3
- 0003476436
- 2nd ed, Cornils, B, Herrmann, W. A, Eds, Wiley-VCH: Weinheim
- (c) Aqueous-Phase Organometallic Catalysis: Concepts and Applications, 2nd ed.; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 2004.
- (2004) Aqueous-Phase Organometallic Catalysis: Concepts and Applications

4
- 59849105208
- Organic Reactions in Water; Lindstrom, U. M., Eds.; Blackwell Publishing Ltd.: Oxford, 2007.
- (d) Organic Reactions in Water; Lindstrom, U. M., Eds.; Blackwell Publishing Ltd.: Oxford, 2007.

5
- 0032580376
- (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
- (1998) Tetrahedron , vol.54 , pp. 4413-4450
- Grubbs, R.H.¹ Chang, S.²

6
- 0001399412
- (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
- (2000) Angew. Chem., Int. Ed , vol.39 , pp. 3012-3043
- Fürstner, A.¹

7
- 0034746687
- (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
- (2001) Acc. Chem. Res , vol.34 , pp. 18-29
- Trnka, T.M.¹ Grubbs, R.H.²

8
- 0142023994
- (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633.
- (2003) Angew. Chem., Int. Ed , vol.42 , pp. 4592-4633
- Schrock, R.R.¹ Hoveyda, A.H.²

9
- 0038215596
- (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923.
- (2003) Angew. Chem., Int. Ed , vol.42 , pp. 1900-1923
- Connon, S.J.¹ Blechert, S.²

10
- 1442360753
- Grubbs, R. H, Ed, Wiley-VCH: Weinheim
- (f) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003.
- (2003) Handbook of Metathesis

11
- 2942589152
- (g) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238.
- (2004) Chem. Rev , vol.104 , pp. 2199-2238
- Deiters, A.¹ Martin, S.F.²

12
- 22744448499
- (h) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490-4527.
- (2005) Angew. Chem., Int. Ed , vol.44 , pp. 4490-4527
- Nicolaou, K.C.¹ Bulger, P.G.² Sarlah, D.³

13
- 33749026617
- (i) Gradillas, A.; Perez-Castells, J. Angew. Chem., Int. Ed. 2006, 45, 6086-6101.
- (2006) Angew. Chem., Int. Ed , vol.45 , pp. 6086-6101
- Gradillas, A.¹ Perez-Castells, J.²

14
- 34248327589
- (j) Schrodi, Y.; Pederson, R. L. Aldrichim. Acta 2007, 40, 45-52.
- (2007) Aldrichim. Acta , vol.40 , pp. 45-52
- Schrodi, Y.¹ Pederson, R.L.²

15
- 34548728077
- (a) Clavier, H.; Grela, K.; Kirschning, A.; Mauduit, M.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 6786-6801.
- (2007) Angew. Chem., Int. Ed , vol.46 , pp. 6786-6801
- Clavier, H.¹ Grela, K.² Kirschning, A.³ Mauduit, M.⁴ Nolan, S.P.⁵

16
- 36348949214
- (b) Binder, J. B.; Blank, J. J.; Raines, R. T. Org. Lett. 2007, 9, 4885-4888.
- (2007) Org. Lett , vol.9 , pp. 4885-4888
- Binder, J.B.¹ Blank, J.J.² Raines, R.T.³

17
- 33750973062
- (c) Mwangi, M. T.; Runge, M. B.; Bowden, N. B. J. Am. Chem. Soc. 2006, 128, 14434-14435.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 14434-14435
- Mwangi, M.T.¹ Runge, M.B.² Bowden, N.B.³

18
- 4243081008
- (a) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317-4325.
- (1996) Organometallics , vol.15 , pp. 4317-4325
- Mohr, B.¹ Lynn, D.M.² Grubbs, R.H.³

19
- 0032567497
- (b) Kirkland, T. A.; Lynn, D. M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 9904-9909.
- (1998) J. Org. Chem , vol.63 , pp. 9904-9909
- Kirkland, T.A.¹ Lynn, D.M.² Grubbs, R.H.³

20
- 0034827922
- (c) Lynn, D. M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 3187-3193.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 3187-3193
- Lynn, D.M.¹ Grubbs, R.H.²

21
- 0034686682
- Lynn, D. M.; Mohr, B.; Grubbs, R. H.; Henling, L. M.; Day, M. W. J. Am. Chem. Soc. 2000, 122, 6601-6609.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 6601-6609
- Lynn, D.M.¹ Mohr, B.² Grubbs, R.H.³ Henling, L.M.⁴ Day, M.W.⁵

22
- 33645394125
- Hong, S. H.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 3508-3509.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 3508-3509
- Hong, S.H.¹ Grubbs, R.H.²

23
- 33746823357
- (a) Michrowska, A.; Gulajski, L.; Kaczmarska, Z.; Mennecke, K.; Kirschning, A.; Grela, K. Green Chem. 2006, 8, 685-688.
- (2006) Green Chem , vol.8 , pp. 685-688
- Michrowska, A.¹ Gulajski, L.² Kaczmarska, Z.³ Mennecke, K.⁴ Kirschning, A.⁵ Grela, K.⁶

24
- 34447302076
- (b) Jordan, J. P.; Grubbs, R. H. Angew. Chem., Int. Ed. 2007, 46, 5152-5155.
- (2007) Angew. Chem., Int. Ed , vol.46 , pp. 5152-5155
- Jordan, J.P.¹ Grubbs, R.H.²

25
- 0043194171
- Chatterjee, A. K.; Choi, T-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 11360-11370
- Chatterjee, A.K.¹ Choi, T.-L.² Sanders, D.P.³ Grubbs, R.H.⁴

26
- 0033598258
- Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
- (1999) Org. Lett , vol.1 , pp. 953-956
- Scholl, M.¹ Ding, S.² Lee, C.W.³ Grubbs, R.H.⁴

27
- 0033518572
- (a) Kingsbury, J. S.; Harrity, J. P. A.; Bonetatebus, P. J., Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791-799.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 791-799
- Kingsbury, J.S.¹ Harrity, J.P.A.² Bonetatebus Jr., P.J.³ Hoveyda, A.H.⁴

28
- 0034734340
- (b) Garber, S. B.; Kingsbury, J. S.; Grey, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 8168-8179
- Garber, S.B.¹ Kingsbury, J.S.² Grey, B.L.³ Hoveyda, A.H.⁴

29
- 0034676688
- (c) Gessler, S.; Randl, S.; Blechert, S. Tetrahedron Lett. 2000, 41, 9973-9976.
- (2000) Tetrahedron Lett , vol.41 , pp. 9973-9976
- Gessler, S.¹ Randl, S.² Blechert, S.³

30
- 0037021049
- (d) Grela, K.; Haruyunyan, S.; Michrowska, A. Angew. Chem., Int. Ed. 2002, 41, 4038-4040.
- (2002) Angew. Chem., Int. Ed , vol.41 , pp. 4038-4040
- Grela, K.¹ Haruyunyan, S.² Michrowska, A.³

31
- 3342982883
- (e) Michrowska, A.; Bujok, R.; Harutyunyan, S.; Sashuk, V.; Dolgonos, G.; Grela, K. J. Am. Chem. Soc. 2004, 126, 9318-9325.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 9318-9325
- Michrowska, A.¹ Bujok, R.² Harutyunyan, S.³ Sashuk, V.⁴ Dolgonos, G.⁵ Grela, K.⁶

32
- 0037007937
- (f) Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 2403-2405.
- (2002) Angew. Chem., Int. Ed , vol.41 , pp. 2403-2405
- Wakamatsu, H.¹ Blechert, S.²

33
- 34250325511
- (g) Deshmukh, P. H.; Blechert, S. Dalton Trans. 2007, 2479-2491.
- (2007) Dalton Trans , pp. 2479-2491
- Deshmukh, P.H.¹ Blechert, S.²

34
- 56549089327
- Water-Soluble Compositions of Bioactive Lipophilic Compounds
- U.S. Patent 6,045,826, Apr 4
- (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.
- (2000)
- Borowy-Borowski, H.¹ Sikorska-Walker, M.² Walker, P.R.³

35
- 56549089327
- Water-Soluble Compositions of Bioactive Lipophilic Compounds
- U.S. Patent 6,191,172, Feb 20
- (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.
- (2001)
- Borowy-Borowski, H.¹ Sikorska-Walker, M.² Walker, P.R.³

36
- 56549089327
- Water-Soluble Compositions of Bioactive Lipophilic Compounds
- U.S. Patent 6,632,443, Oct 14
- (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.
- (2003)
- Borowy-Borowski, H.¹ Sikorska-Walker, M.² Walker, P.R.³

37
- 33746236970
- (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. 1995, 34, 2039-2041.
- (1995) Angew. Chem., Int. Ed , vol.34 , pp. 2039-2041
- Schwab, P.¹ France, M.B.² Ziller, J.W.³ Grubbs, R.H.⁴

38
- 0001855961
- (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
- (1996) J. Am. Chem. Soc , vol.118 , pp. 100-110
- Schwab, P.¹ Grubbs, R.H.² Ziller, J.W.³

39
- 59849096408
- accessed August 2007
- 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).
- PCI-102B Eastman Vitamin E TPGS NF - Applications and Properties

40
- 59849116976
- Sigma-Aldrich catalog nos. (a) 234729, (b) P4391, (c) 202401, (d) L3771.
- Sigma-Aldrich catalog nos. (a) 234729, (b) P4391, (c) 202401, (d) L3771.

41
- 20344388819
- Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolib, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275-3279.
- (2005) Angew. Chem., Int. Ed , vol.44 , pp. 3275-3279
- Narayan, S.¹ Muldoon, J.² Finn, M.G.³ Fokin, V.V.⁴ Kolib, H.C.⁵ Sharpless, K.B.⁶

42
- 34250726521
- See also
- See also: Blackmond, D. G.; Armstrong, A.; Coombe, V.; Wells, A. Angew. Chem., Int. Ed. 2007, 46, 3798-3800.
- (2007) Angew. Chem., Int. Ed , vol.46 , pp. 3798-3800
- Blackmond, D.G.¹ Armstrong, A.² Coombe, V.³ Wells, A.⁴

43
- 0035944467
- Choi, T-L.; Lee, C. W.; Chatterjee, A. K.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 10417-10418.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 10417-10418
- Choi, T.-L.¹ Lee, C.W.² Chatterjee, A.K.³ Grubbs, R.H.⁴

44
- 0034685462
- Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783-3784.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 3783-3784
- Chatterjee, A.K.¹ Morgan, J.P.² Scholl, M.³ Grubbs, R.H.⁴

45
- 59849112417
- See the experimental procedure below and those in the Supporting Information
- See the experimental procedure below and those in the Supporting Information.

46
- 0037009018
- Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 3171-3174.
- (2002) Angew. Chem., Int. Ed , vol.41 , pp. 3171-3174
- Chatterjee, A.K.¹ Grubbs, R.H.²

47
- 85034336744
- (a) Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 4035-4037.
- (2002) Angew. Chem., Int. Ed , vol.41 , pp. 4035-4037
- Love, J.A.¹ Morgan, J.P.² Trnka, T.M.³ Grubbs, R.H.⁴

48
- 0037716294
- (b) Rivard, M.; Blechert, S. Eur. J. Org. Chem. 2003, 2225-2228.
- (2003) Eur. J. Org. Chem , pp. 2225-2228
- Rivard, M.¹ Blechert, S.²

49
- 0035929110
- Randl, S.; Connon, S. J.; Blechert, S. Chem. Commun. 2001, 1796-1797.
- (2001) Chem. Commun , pp. 1796-1797
- Randl, S.¹ Connon, S.J.² Blechert, S.³

50
- 48949099423
- (a) Lipshutz, B. H.; Taft, B. R. Org. Lett. 2008, 10, 1329-1332.
- (2008) Org. Lett , vol.10 , pp. 1329-1332
- Lipshutz, B.H.¹ Taft, B.R.²

51
- 48949100374
- (b) Lipshutz, B. H.; Petersen, T. B.; Abela, A. R. Org. Lett. 2008, 10, 1333-1336.
- (2008) Org. Lett , vol.10 , pp. 1333-1336
- Lipshutz, B.H.¹ Petersen, T.B.² Abela, A.R.³

52
- 0000080480
- (a) Griffin, W. C. J. Soc. Sosmet. Chem. 1949, 1, 311-326.
- (1949) J. Soc. Sosmet. Chem , vol.1 , pp. 311-326
- Griffin, W.C.¹

53
- 7444226991
- (b) Niraula, B. B.; Chun, T. K.; Othman, H.; Misran, M. Colloids Surf. A 2004, 248, 157-166.
- (2004) Colloids Surf. A , vol.248 , pp. 157-166
- Niraula, B.B.¹ Chun, T.K.² Othman, H.³ Misran, M.⁴

54
- 59849118320
- 11 a complete understanding of the roles of its various ingredients, including impurities (e.g., PEG diesters, etc.) in micelle formation remains to be elucidated.
- 11 a complete understanding of the roles of its various ingredients, including impurities (e.g., PEG diesters, etc.) in micelle formation remains to be elucidated.

55
- 59849109537
- Representative procedure for olefin CM (Table 2, entry 8, 10-Undecenol (94.8 mg, 0.556 mmol, tert-butyl acrylate (159.5 mg, 1.24 mmol, and Grubbs second-generation catalyst 7b (9.9 mg, 0.0116 mmol) were sequentially added to a Teflon-coated, stir bar containing Biotage 2-5 mL microwave reactor vial at room temperature and sealed with a septum. An aliquot of PTS/H2O (1.0 mL; 2.5% PTS by weight; all cross-coupling reactions were conducted at 0.5 M unless stated otherwise) was added via syringe, and the resulting emulsion was allowed to stir at rt for 12 h. The homogeneous reaction mixture was then diluted with EtOAc (5 mL) and filtered through a bed of silica gel layered over Celite, and the bed was washed (3 x 10 mL) with EtOAc. The volatiles were removed in vacuo to afford the crude material, which was subsequently purified by flash chromatography on silica gel (eluting with 10% EtOAc/hexanes) to yield the product as a colorless oil 123 mg, 82, The report
- + ) 271.2273, found 271.2282.

56
- 59849110918
- 2O in May, 2008 (catalog #698717).
- 2O in May, 2008 (catalog #698717).

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