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Synlett

Volumn , Issue 12, 2008, Pages 1781-1784

Palladium N-heterocyclic carbene catalysts for synthesis of diaryl ethers

(4) Akkoç, Mitat a Gürbüz, Nevin a Çetinkaya, Engin b Özdemir, Ismail a

a INONU UNIVERSITY (Turkey)

b EGE UNIVERSITY (Turkey)

Author keywords

C O bond formation; Etherification; N heterocyclic carbene; Palladium coupling

Indexed keywords

1,3 DIALKYLIMIDAZOLINIUM; BENZALDEHYDE DERIVATIVE; CARBENOID; DIARYL ETHER DERIVATIVE; ETHER DERIVATIVE; IMIDAZOLE DERIVATIVE; N HETEROCYCLIC CARBENE; PALLADIUM;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; ETHERIFICATION; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 48349096167 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078548 Document Type: Article

Times cited : (17)

References (54)

1
- 0008165462
- (a) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
- (1999) J. Organomet. Chem , vol.576 , pp. 125
- Yang, B.H.¹ Buchwald, S.L.²

2
- 0032541260
- (b) Hartwig, J. F. Angew Chem. Int. Ed. 1998, 37, 2046.
- (1998) Angew Chem. Int. Ed , vol.37 , pp. 2046
- Hartwig, J.F.¹

3
- 0033549741
- Theil, F. Angew. Chem. Int. Ed. 1999, 38, 2345.
- (1999) Angew. Chem. Int. Ed , vol.38 , pp. 2345
- Theil, F.¹

4
- 84979085204
- Ullmann, F. Chem. Ber. 1904, 37, 853.
- (1904) Chem. Ber , vol.37 , pp. 853
- Ullmann, F.¹

5
- 0345329013
- Lindley, J. Tetrahedron 1984, 40, 1433.
- (1984) Tetrahedron , vol.40 , pp. 1433
- Lindley, J.¹

6
- 33746659068
- (a) Frlan, R.; Kikelj, D. Synthesis 2006, 2271.
- (2006) Synthesis , pp. 2271
- Frlan, R.¹ Kikelj, D.²

7
- 9644277114
- (b) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
- (2004) Coord. Chem. Rev , vol.248 , pp. 2337
- Beletskaya, I.P.¹ Cheprakov, A.V.²

8
- 0346749657
- (c) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428.
- (2003) Synlett , pp. 2428
- Kunz, K.¹ Scholz, U.² Ganzer, D.³

9
- 34548462479
- Ouali, A.; Spindler, J.-F.; Jutand, A.; Taillefer, M. Adv. Synth. Catal. 2007, 349, 1906.
- (2007) Adv. Synth. Catal , vol.349 , pp. 1906
- Ouali, A.¹ Spindler, J.-F.² Jutand, A.³ Taillefer, M.⁴

10
- 0037007703
- (a) Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623.
- (2002) Org. Lett , vol.4 , pp. 1623
- Buck, E.¹ Song, Z.J.² Tschaen, D.³ Dormer, P.G.⁴ Volante, R.P.⁵ Reider, P.J.⁶

11
- 0034613228
- (b) Wipf, P.; Jung, J. K. J. Org. Chem. 2000, 65, 6319.
- (2000) J. Org. Chem , vol.65 , pp. 6319
- Wipf, P.¹ Jung, J.K.²

12
- 33751426162
- (c) Miao, T.; Wang, L. Tetrahedron Lett. 2007, 48, 95.
- (2007) Tetrahedron Lett , vol.48 , pp. 95
- Miao, T.¹ Wang, L.²

13
- 33947604002
- (d) Lipshutz, B. H.; Unger, J. B.; Taft, B. R. Org. Lett. 2007, 9, 1089.
- (2007) Org. Lett , vol.9 , pp. 1089
- Lipshutz, B.H.¹ Unger, J.B.² Taft, B.R.³

14
- 33746311445
- (e) Cai, Q.; Zou, B. L.; Ma, D. W. Angew. Chem. 2006, 118, 1298.
- (2006) Angew. Chem , vol.118 , pp. 1298
- Cai, Q.¹ Zou, B.L.² Ma, D.W.³

15
- 0041409634
- (f) Luo, Y. T.; Wu, J. X.; Ren, R. X. Synlett 2003, 1734.
- (2003) Synlett , pp. 1734
- Luo, Y.T.¹ Wu, J.X.² Ren, R.X.³

16
- 0034840318
- (g) Gujadhur, R.; Venkataraman, D. Synth. Commun. 2001, 31, 2865.
- (2001) Synth. Commun , vol.31 , pp. 2865
- Gujadhur, R.¹ Venkataraman, D.²

17
- 0030700314
- (h) Marcoux, J. F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 10539
- Marcoux, J.F.¹ Doye, S.² Buchwald, S.L.³

18
- 0033617396
- (i) Kalinin, A. V.; Bower, J. F.; Riebel, P.; Snieckus, V. J. Org. Chem. 1999, 64, 2986.
- (1999) J. Org. Chem , vol.64 , pp. 2986
- Kalinin, A.V.¹ Bower, J.F.² Riebel, P.³ Snieckus, V.⁴

19
- 0001199033
- (j) Paine, A. J. J. Am. Chem. Soc. 1987, 109, 1496.
- (1987) J. Am. Chem. Soc , vol.109 , pp. 1496
- Paine, A.J.¹

20
- 0033531744
- (a) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 3224
- Mann, G.¹ Incarvito, C.² Rheingold, A.L.³ Hartwig, J.F.⁴

21
- 0033549049
- (b) Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 4369
- Aranyos, A.¹ Old, D.W.² Kiyomori, A.³ Wolfe, J.P.⁴ Sadighi, J.P.⁵ Buchwald, S.L.⁶

22
- 17044401299
- (c) Harkal, S.; Kumar, K.; Michalik, D.; Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Beller, M. Tetrahedron Lett. 2005, 46, 3237.
- (2005) Tetrahedron Lett , vol.46 , pp. 3237
- Harkal, S.¹ Kumar, K.² Michalik, D.³ Zapf, A.⁴ Jackstell, R.⁵ Rataboul, F.⁶ Riermeier, T.⁷ Monsees, A.⁸ Beller, M.⁹

23
- 0030466983
- (a) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 13109.
- (1996) J. Am. Chem. Soc , vol.118 , pp. 13109
- Mann, G.¹ Hartwig, J.F.²

24
- 0030958369
- (b) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 3395
- Palucki, M.¹ Wolfe, J.P.² Buchwald, S.L.³

25
- 0030780953
- (c) Mann, G.; Hartwig, J. F. Tetrahedron Lett. 1997, 38, 8005.
- (1997) Tetrahedron Lett , vol.38 , pp. 8005
- Mann, G.¹ Hartwig, J.F.²

26
- 0000412744
- Cornils, B, Herrmann, W. A, Eds, Wiley-VCH: Weinheim
- Herrmann, W. A. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B.; Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1996, 712.
- (1996) Applied Homogeneous Catalysis with Organometallic Compounds , pp. 712
- Herrmann, W.A.¹

27
- 0002138516
- (a) Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
- (2000) Chem. Rev , vol.100 , pp. 39
- Bourissou, D.¹ Guerret, O.² Gabbai, F.P.³ Bertrand, G.⁴

28
- 33745118388
- (b) Hahn, F. E. Angew. Chem. Int. Ed. 2006, 45, 1348.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 1348
- Hahn, F.E.¹

29
- 0037090932
- (c) Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290.
- (2002) Angew. Chem. Int. Ed , vol.41 , pp. 1290
- Herrmann, W.A.¹

30
- 9644254490
- (d) Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 248, 2239.
- (2004) Coord. Chem. Rev , vol.248 , pp. 2239
- Peris, E.¹ Crabtree, R.H.²

31
- 33846821468
- (a) Dragutan, V.; Dragutan, I.; Delaude, L.; Demonceau, A. Coord. Chem. Rev. 2007, 251, 765.
- (2007) Coord. Chem. Rev , vol.251 , pp. 765
- Dragutan, V.¹ Dragutan, I.² Delaude, L.³ Demonceau, A.⁴

32
- 33846882367
- (b) Lin, I. J. B.; Vasam, C. S. Coord. Chem. Rev. 2007, 251, 642.
- (2007) Coord. Chem. Rev , vol.251 , pp. 642
- Lin, I.J.B.¹ Vasam, C.S.²

33
- 33846797894
- (c) Gonzalez, S. D.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874.
- (2007) Coord. Chem. Rev , vol.251 , pp. 874
- Gonzalez, S.D.¹ Nolan, S.P.²

34
- 33750296864
- (d) Yen, S. K.; Koh, L. L.; Hahn, F. E.; Huynh, H. V.; Hor, T. S. A. Organometallics 2006, 25, 5105.
- (2006) Organometallics , vol.25 , pp. 5105
- Yen, S.K.¹ Koh, L.L.² Hahn, F.E.³ Huynh, H.V.⁴ Hor, T.S.A.⁵

35
- 33846254035
- (a) Hahn, F. E.; Jahnke, M. C.; Pape, T. Organometallics 2007, 26, 150.
- (2007) Organometallics , vol.26 , pp. 150
- Hahn, F.E.¹ Jahnke, M.C.² Pape, T.³

36
- 27844602946
- (b) Lavallo, V.; Canac, Y.; DeHope, A.; Donnadieu, B.; Bertrand, G. Angew. Chem. Int. Ed. 2005, 44, 7236.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 7236
- Lavallo, V.¹ Canac, Y.² DeHope, A.³ Donnadieu, B.⁴ Bertrand, G.⁵

37
- 24944490141
- (c) Lavallo, V.; Canac, Y.; Prasang, C.; Donnadieu, B.; Bertrand, G. Angew. Chem. Int. Ed. 2005, 44, 5705.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 5705
- Lavallo, V.¹ Canac, Y.² Prasang, C.³ Donnadieu, B.⁴ Bertrand, G.⁵

38
- 33947241996
- (a) Nishioka, T.; Shibata, T.; Kinoshita, I. Organometallics 2007, 26, 1126.
- (2007) Organometallics , vol.26 , pp. 1126
- Nishioka, T.¹ Shibata, T.² Kinoshita, I.³

39
- 33947164329
- (b) Gnanamgari, D.; Moores, A.; Rajaseelan, E.; Crabtree, R. H. Organometallics 2007, 26, 1226.
- (2007) Organometallics , vol.26 , pp. 1226
- Gnanamgari, D.¹ Moores, A.² Rajaseelan, E.³ Crabtree, R.H.⁴

40
- 0035912006
- (c) Rüther, T.; Braussaud, N.; Cavell, K. J. Organometallics 2001, 20, 1247.
- (2001) Organometallics , vol.20 , pp. 1247
- Rüther, T.¹ Braussaud, N.² Cavell, K.J.³

41
- 0000934713
- (a) McGuinness, D. S.; Mueller, W.; Wasserscheid, W. P.; Cavell, K. J.; Skelton, B. W.; White, A. H.; Englert, U. Organometallics 2002, 21, 175.
- (2002) Organometallics , vol.21 , pp. 175
- McGuinness, D.S.¹ Mueller, W.² Wasserscheid, W.P.³ Cavell, K.J.⁴ Skelton, B.W.⁵ White, A.H.⁶ Englert, U.⁷

42
- 33749872034
- (b) Nielsen, D. J.; Cavell, K. J.; Skelton, B. W.; White, A. H. Organometallics 2006, 25, 4850.
- (2006) Organometallics , vol.25 , pp. 4850
- Nielsen, D.J.¹ Cavell, K.J.² Skelton, B.W.³ White, A.H.⁴

43
- 34748830314
- (c) Iglesias, M.; Beetstra, D. J.; Stasch, A.; Horton, P. N.; Hursthouse, M. B.; Coles, S. J.; Cavell, K. J.; Devrisi, A.; Fallis, I. A. Organometallics 2007, 26, 4800.
- (2007) Organometallics , vol.26 , pp. 4800
- Iglesias, M.¹ Beetstra, D.J.² Stasch, A.³ Horton, P.N.⁴ Hursthouse, M.B.⁵ Coles, S.J.⁶ Cavell, K.J.⁷ Devrisi, A.⁸ Fallis, I.A.⁹

44
- 0038159899
- Böhm, V. P. W.; Gstöttmayr, C. W. K.; Herrmann, W. A. J. Organomet. Chem. 2000, 595, 186.
- (2000) J. Organomet. Chem , vol.595 , pp. 186
- Böhm, V.P.W.¹ Gstöttmayr, C.W.K.² Herrmann, W.A.³

45
- 10944232581
- (a) Özdemir, İ.; Gök, Y.; Gürbüz, N.; Yaşar, S.; Çetinkaya, E.; Çetinkaya, B. Polish J. Chem. 2004, 78, 2141.
- (2004) Polish J. Chem , vol.78 , pp. 2141
- Özdemir, I.¹ Gök, Y.² Gürbüz, N.³ Yaşar, S.⁴ Çetinkaya, E.⁵ Çetinkaya, B.⁶

46
- 8644290061
- (b) Özdemir, İ.; Gök, Y.; Gürbüz, N.; Çetinkaya, E.; Çetinkaya, B. Synth. Commun. 2004, 34, 4135.
- (2004) Synth. Commun , vol.34 , pp. 4135
- Özdemir, I.¹ Gök, Y.² Gürbüz, N.³ Çetinkaya, E.⁴ Çetinkaya, B.⁵

47
- 2542489193
- (c) Özdemir, İ.; Alici, B.; Gürbüz, N.; Çetinkaya, E.; Çetinkaya, B. J. Mol. Catal. A: Chem. 2004, 217, 37.
- (2004) J. Mol. Catal. A: Chem , vol.217 , pp. 37
- Özdemir, I.¹ Alici, B.² Gürbüz, N.³ Çetinkaya, E.⁴ Çetinkaya, B.⁵

48
- 38649141502
- Özdemir, İ.; Demir, S.; Çetinkaya, B.; Gourlaouen, C.; Maseras, F.; Bruneau, C.; Dixneuf, P. H. J. Am. Chem. Soc. 2008, 130, 1156.
- (2008) J. Am. Chem. Soc , vol.130 , pp. 1156
- Özdemir, I.¹ Demir, S.² Çetinkaya, B.³ Gourlaouen, C.⁴ Maseras, F.⁵ Bruneau, C.⁶ Dixneuf, P.H.⁷

49
- 70350133137
- Çetinkaya, E.; Hitchcock, P. B.; Jasim, H. A.; Lappert, M. F.; Spyropoulos, K. J. Chem. Soc., Perkin Trans. 1 1992, 56.
- (1992) J. Chem. Soc., Perkin Trans. 1 , pp. 56
- Çetinkaya, E.¹ Hitchcock, P.B.² Jasim, H.A.³ Lappert, M.F.⁴ Spyropoulos, K.⁵

50
- 48349087794
- General Procedure for the Synthesis of 1,3-Dialkyl-imidazolinium Bromides 2: To a solution of 1-(methoxyethyl)imidazoline (1 mmol) in DMF (3 mL, alkyl halide (1.1 mmol) was added and the resulting solution was stirred for 1 h at r.t. and heated for 12 h at 80°C Et2O (10 mL) was added to the reaction mixture. A white solid was precipitated in this period. The precipitate was then crystallized from EtOH-Et2O (1:2, 1-(2-Methoxyethyl)-3-(cyclohexylmethyl)imidazolinium Bromide (2a, yield: 2.65 g (87, mp 29°C. IR: 1465 (C=N) cm-1. 1H NMR (300.13 MHz, CDCl3, δ, 3.11 (s, 3 H, OMe, 3.38 (t, J, 4.8 Hz, 2 H, NCH2CH2O, 3.59 (t, J, 4.8 Hz, 2 H, NCH2CH2O, 3.79, 3.89 (m, 4 H, NCH 2CH2N, 0.72-1.41 (m, 11 H, CH2C 6H11, 3.15 d, 2 H, CH2C 6H11
- 2O, filtered through a pad of silica gel with copious washings, concentrated and purified by flash chromatography on silica gel. The purity of the compounds was checked by GC and yields are based on the aryl chloride.

51
- 12844271107
- (a) Özdemir, İ.; Demir, S.; Yaşar, S.; Çetinkaya, B. Appl. Organomet. Chem. 2005, 19, 55.
- (2005) Appl. Organomet. Chem , vol.19 , pp. 55
- Özdemir, I.¹ Demir, S.² Yaşar, S.³ Çetinkaya, B.⁴

52
- 33645782787
- (b) Demir, S.; Özdemir, İ.; Çetinkaya, B. Appl. Organomet. Chem. 2006, 20, 254.
- (2006) Appl. Organomet. Chem , vol.20 , pp. 254
- Demir, S.¹ Özdemir, I.² Çetinkaya, B.³

53
- 34247193561
- (c) Özdemir, İ.; Demir, S.; Çetinkaya, B. Synlett 2007, 889.
- (2007) Synlett , pp. 889
- Özdemir, I.¹ Demir, S.² Çetinkaya, B.³

54
- 14744296117
- (d) Gürbüz, N.; Özdemir, İ.; Çetinkaya, B. Tetrahedron Lett. 2005, 46, 2273.
- (2005) Tetrahedron Lett , vol.46 , pp. 2273
- Gürbüz, N.¹ Özdemir, I.² Çetinkaya, B.³

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