SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 4, 2008, Pages 561-564

Synthesis of silole skeletons via metathesis reactions

(3) Matsuda, Takanori a Yamaguchi, Yoshiyuki a Murakami, Masahiro a

a KYOTO UNIVERSITY (Japan)

Author keywords

Metathesis; Molybdenum; Ring closure; Ruthenium; Silole

Indexed keywords

2 ALKENYL 1 SILAINDENE; ALKADIENE; ALKENE; ALKENE DERIVATIVE; ALKYNE; RUTHENIUM; SILICON; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; RING CLOSING METATHESIS; SKELETON; SYNTHESIS;

EID: 40949135376 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1032096 Document Type: Article

Times cited : (34)

References (48)

1
- 28244440935
- (a) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
- (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 371
- Armstrong, S.K.¹

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

3
- 0001399412
- (c) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
- (2000) Angew. Chem. Int. Ed , vol.39 , pp. 3012
- Fürstner, A.¹

4
- 0142023994
- (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2003, 42, 4592.
- (2003) Angew. Chem. Int. Ed , vol.42 , pp. 4592
- Schrock, R.R.¹ Hoveyda, A.H.²

5
- 1442360753
- Grubbs, R. H, Ed, Wiley-VCH: Weinheim
- (e) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003.
- (2003) Handbook of Metathesis

6
- 2942589152
- (f) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199.
- (2004) Chem. Rev , vol.104 , pp. 2199
- Deiters, A.¹ Martin, S.F.²

7
- 2942609172
- (g) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239.
- (2004) Chem. Rev , vol.104 , pp. 2239
- McReynolds, M.D.¹ Dougherty, J.M.² Hanson, P.R.³

8
- 0030771019
- (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036.
- (1997) Angew. Chem., Int. Ed. Engl , vol.36 , pp. 2036
- Schuster, M.¹ Blechert, S.²

9
- 0001399412
- (b) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
- (2000) Angew. Chem. Int. Ed , vol.39 , pp. 3012
- Fürstner, A.¹

10
- 0141925985
- (c) Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693.
- (2003) Eur. J. Org. Chem , pp. 3693
- Felpin, F.-X.¹ Lebreton, J.²

11
- 22744448499
- (d) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4490.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 4490
- Nicolaou, K.C.¹ Bulger, P.G.² Sarlah, D.³

12
- 33748511666
- For reviews, see: a
- For reviews, see: (a) Yamaguchi, S.; Tamao, K. J. Chem. Soc., Dalton Trans. 1998, 3693.
- (1998) J. Chem. Soc., Dalton Trans , pp. 3693
- Yamaguchi, S.¹ Tamao, K.²

13
- 0242352408
- (b) Hissler, M.; Dyer, P. W.; Réau, R. Coord. Chem. Rev. 2003, 244, 1.
- (2003) Coord. Chem. Rev , vol.244 , pp. 1
- Hissler, M.¹ Dyer, P.W.² Réau, R.³

14
- 12444335750
- For recent reviews, see: a
- For recent reviews, see: (a) Hughes, G.; Bryce, M. R. J. Mater. Chem. 2005, 15, 94.
- (2005) J. Mater. Chem , vol.15 , pp. 94
- Hughes, G.¹ Bryce, M.R.²

15
- 8444245574
- (b) Kulkarni, A. P.; Tonzola, C. J.; Babel, A.; Jenekhe, S. A. Chem. Mater. 2004, 16, 4556.
- (2004) Chem. Mater , vol.16 , pp. 4556
- Kulkarni, A.P.¹ Tonzola, C.J.² Babel, A.³ Jenekhe, S.A.⁴

16
- 34248578376
- (c) Shirota, Y.; Kageyama, H. Chem. Rev. 2007, 107, 953.
- (2007) Chem. Rev , vol.107 , pp. 953
- Shirota, Y.¹ Kageyama, H.²

17
- 33846421611
- (a) Matsuda, T.; Kadowaki, S.; Goya, T.; Murakami, M. Org. Lett. 2007, 9, 133.
- (2007) Org. Lett , vol.9 , pp. 133
- Matsuda, T.¹ Kadowaki, S.² Goya, T.³ Murakami, M.⁴

18
- 34250757094
- (b) Matsuda, T.; Kadowaki, S.; Murakami, M. Chem. Commun. 2007, 2627.
- (2007) Chem. Commun , pp. 2627
- Matsuda, T.¹ Kadowaki, S.² Murakami, M.³

19
- 0000498386
- For synthesis of other heteroles by RCM, see: a
- For synthesis of other heteroles by RCM, see: (a) Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029.
- (1994) J. Org. Chem , vol.59 , pp. 4029
- Fujimura, O.¹ Fu, G.C.² Grubbs, R.H.³

20
- 0037122126
- (b) Arisawa, M.; Terada, Y.; Nakagawa, M.; Nishida, A. Angew. Chem. Int. Ed. 2002, 41, 4732.
- (2002) Angew. Chem. Int. Ed , vol.41 , pp. 4732
- Arisawa, M.¹ Terada, Y.² Nakagawa, M.³ Nishida, A.⁴

21
- 21844455311
- (c) van Otterlo, W. A. L.; Morgans, G. L.; Madeley, L. G.; Kuzvidza, S.; Moleele, S. S.; Thornton, N.; de Koning, C. B. Tetrahedron 2005, 61, 7746.
- (2005) Tetrahedron , vol.61 , pp. 7746
- van Otterlo, W.A.L.¹ Morgans, G.L.² Madeley, L.G.³ Kuzvidza, S.⁴ Moleele, S.S.⁵ Thornton, N.⁶ de Koning, C.B.⁷

22
- 7044241256
- For RCM forming aromatic compounds, see: d
- For RCM forming aromatic compounds, see: (d) Iuliano, A.; Piccioli, P.; Fabbri, D. Org. Lett. 2004, 6, 3711.
- (2004) Org. Lett , vol.6 , pp. 3711
- Iuliano, A.¹ Piccioli, P.² Fabbri, D.³

23
- 26844488768
- (e) Bonifacio, M. C.; Robertson, C. R.; Jung, J.-Y.; King, B. T. J. Org. Chem. 2005, 70, 8522.
- (2005) J. Org. Chem , vol.70 , pp. 8522
- Bonifacio, M.C.¹ Robertson, C.R.² Jung, J.-Y.³ King, B.T.⁴

24
- 33746216313
- For a review, see: f
- For a review, see: (f) Donohoe, T. J.; Orr, A. J.; Bingham, M. Angew. Chem. Int. Ed. 2006, 45, 2664.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 2664
- Donohoe, T.J.¹ Orr, A.J.² Bingham, M.³

25
- 40949123290
- Preparation of Siladienes 1 Dimethyl(1-phenylvinyl)(2-vinylphenyl) silane (1a) To a solution of chlorodimethyl(2-vinylphenyl)silane (2.0 g, 10.2 mmol) in THF (10 mL) was added a solution of (1-phenylvinyl)magnesium bromide in THF, which was prepared from a-bromostyrene (5.0 g, 27.3 mmol) and Mg (0.68 g, 28 mmol) in THF (20 mL) at r.t. for 3 h, at 0°C. After the mixture was stirred at r.t. for 10 h, the volatile materials were removed under reduced pressure. The residue was quenched by sat. NH4Cl aq solution, and extracted with hexane. The extract was dried over MgSO4 and concentrated. The residue was purified by column chromatography on silica gel(hexane, Further purification by gel-permeation chromatography (GPC) gave 1a (500 mg, 19, 1H NMR (300 MHz, CDCl3, δ, 0.45 (s, 6 H, 5.22 (dd, J, 11.0, 1.3 Hz, 1 H, 5.61 (dd, J, 17.4, 1.3 Hz, 1 H, 5.69 (d, J, 2.9 Hz, 1 H, 6.01 d, J, 2.9
- 20Ge: 310.0777; found: 310.0786.

26
- 0003357552
- For intermolecular cross-metathesis between vinylsilanes and styrenes, see: a
- For intermolecular cross-metathesis between vinylsilanes and styrenes, see: (a) Pietraszuk, C.; Marciniec, B.; Fischer, H. Organometallics 2000, 19, 913.
- (2000) Organometallics , vol.19 , pp. 913
- Pietraszuk, C.¹ Marciniec, B.² Fischer, H.³

27
- 27744561370
- (b) Pietraszuk, C.; Fischer, H.; Rogalski, S.; Marciniec, B. J. Organomet. Chem. 2005, 690, 5912.
- (2005) J. Organomet. Chem , vol.690 , pp. 5912
- Pietraszuk, C.¹ Fischer, H.² Rogalski, S.³ Marciniec, B.⁴

28
- 35948954822
- (c) Marciniec, B. Acc. Chem. Res. 2007, 40, 943.
- (2007) Acc. Chem. Res , vol.40 , pp. 943
- Marciniec, B.¹

29
- 40949106522
- General Procedure for Ring-Closing Metathesis 1,1-Dimethyl-2-phenyl-1- silaindene(2a)14 To Schrock catalyst (11.5 mg, 0.015 mmol) was added a solution of 1a (76.45 mg, 0.289 mmol) in toluene (5 mL, and the mixture was stirred at r.t. for 2 h. The reaction mixture was taken up with hexane and passed through a pad of Florisil®. Removal of volatile materials afforded 2a (61.4 mg, 0.257 mmol, 89, 1H NMR (300 MHz, CDCl3, δ, 0.48 (s, 6 H, 7.20-7.40 (m, 6 H, 7.49-7.56 (m, 4 H, 13C NMR (75 MHz, CDCl3, δ, 3.1, 124.3, 126.4, 126.6, 127.0, 128.7, 130.0, 131.7, 138.2, 139.0, 141.1, 145.3, 148.8. 29Si NMR (79 MHz, CDCl3, δ, 15.9. HRMS (EI, m/z [M, calcd for C16H16Si: 236.1021; found: 236.1019. 2-(3-Methoxyphenyl)-1,1-dimethyl-1-silaindene (2b) To Grubbs second-generation catalyst (8.7 mg, 0.010 mmol) was added a soluti
- 16Ge: 282.0464; found: 282.0469.

30
- 40949108558
- The inferior results of the reaction of 1d and 1e with Ru-II may be attributed to β-silyl elimination from a ruthenacyclobutane intermediate, which formes a nonalkylidene ruthenium complex that no longer exhibits any RCM activity. See: (a) Pietraszuk, C.; Fischer, H. Chem. Commun. 2000, 2463.
- The inferior results of the reaction of 1d and 1e with Ru-II may be attributed to β-silyl elimination from a ruthenacyclobutane intermediate, which formes a nonalkylidene ruthenium complex that no longer exhibits any RCM activity. See: (a) Pietraszuk, C.; Fischer, H. Chem. Commun. 2000, 2463.

31
- 27744561370
- (b)Pietraszuk, C.; Fischer, H.; Rogalski, S.; Marciniec, B. J. Organomet. Chem. 2005, 690, 5912.
- (2005) J. Organomet. Chem , vol.690 , pp. 5912
- Pietraszuk, C.¹ Fischer, H.² Rogalski, S.³ Marciniec, B.⁴

32
- 40949161519
- Dimethyl(1-phenylvinyl)(2-vinylcyclopent-1-enyl)silane (3a) A solution of (2-vinylcyclopent-1-enyl)lithium in THF, which was prepared from 1-bromo-2-vinylcyclopent-1-ene (0.69 g, 3.99 mmol) and n-BuLi in hexane (1.55 M, 2.8 mL, 4.34 mmol) in THF (10 mL) at -78°C for 1 h, was added to a solution of chlorodimethyl(1-phenylvinyl)silane (0.697 g, 3.54 mmol) in THF (10 mL) at 0°C After the mixture was stirred at r.t. for 10 h, the volatile materials were removed under reduced pressure. The residue was quenched by sat. NH4Cl aq solution, and extracted with hexane. The extract was dried over MgSO4 and concentrated. The residue was purified by column chromatography on silica gel (hexane) to afford 3a (0.32 mg, 32, 1H NMR (300 MHz, CDCl3, δ, 0.29 (s, 6 H, 1.82 (quin, J, 7.5 Hz, 2 H, 2.47-2.60 (m, 4 H, 5.09 (d, J, 10.7 Hz, 1 H, 5.13 (d, J, 17.1 Hz, 1 H, 5.65 d, J, 3.0 Hz, 1 H
- 20Si: 288.1334; found: 288.1330.

33
- 0037244612
- (a) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1.
- (2003) Synthesis , pp. 1
- Poulsen, C.S.¹ Madsen, R.²

34
- 1842483218
- (b) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
- (2004) Chem. Rev , vol.104 , pp. 1317
- Diver, S.T.¹ Giessert, A.J.²

35
- 1542328834
- (c) Mori, M. J. Mol. Catal. A: Chem. 2004, 213, 73.
- (2004) J. Mol. Catal. A: Chem , vol.213 , pp. 73
- Mori, M.¹

36
- 33751225665
- (d) Van de Weghe, P.; Bissert, P.; Blanchard, N.; Eustache, J. J. Organomet. Chem. 2006, 691, 5078.
- (2006) J. Organomet. Chem , vol.691 , pp. 5078
- Van de Weghe, P.¹ Bissert, P.² Blanchard, N.³ Eustache, J.⁴

37
- 33845741583
- (e) Villar, H.; Frings, M.; Bolm, C. Chem. Soc. Rev. 2007, 36, 55.
- (2007) Chem. Soc. Rev , vol.36 , pp. 55
- Villar, H.¹ Frings, M.² Bolm, C.³

38
- 0000340818
- ( 13) For the examples of enyne RCM forming both exo and endo products, see: (a) Kitamura, T.; Sato, Y.; Mori, M. Adv. Synth. Catal. 2002, 344, 678.
- ( 13) For the examples of enyne RCM forming both exo and endo products, see: (a) Kitamura, T.; Sato, Y.; Mori, M. Adv. Synth. Catal. 2002, 344, 678.

39
- 0042626460
- (b) Hansen, E. C.; Lee, D. J. Am. Chem. Soc. 2003, 125, 9582.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 9582
- Hansen, E.C.¹ Lee, D.²

40
- 40949105285
- 1-Dimethyl-2-(pent-1-en-2-yl)-1-silaindene (6) and 1,1-Dimethyl-2-methylene-3-propyl-1,2-dihydro-1-silanaphthalene (7) The title compounds (45.63 mg, 67, 6/7, 50:50) were obtained from enyne RCM of 5 (67.8 mg) using Ru-II. The isomers were separated by HPLC Compound 6: 1H NMR (300 MHz, CDCl3, δ, 0.31 (s, 6 H, 0.97 (t, J, 7.5 Hz, 3 H, 1.59 (sext, J, 7.5 Hz, 2 H, 2.43 (t, J, 7.8 Hz, 2 H, 5.61 (d, J, 1.5 Hz, 1 H, 6.03 (d, J, 1.5 Hz, 1 H, 6.29 (s, 1 H, 7.10-7.20 (m, 2 H, 7.25-7.31 (m, 1 H, 7.48 (d, J, 0.6 Hz, 1 H, 13C NMR (75 MHz, CDCl 3, δ, 1.3, 14.1, 22.4, 35.9, 124.7, 126.0, 128.9, 129.2, 129.6, 133.3, 133.8, 140.2, 141.9, 145.0. HRMS (EI, m/z [M, calcd for C15H20Si: 228.1334; found: 228.1335. Compound 7: 1H NMR (300 MHz, CDCl3, δ, 0.43 (s, 6 H, 1.00 t
- 20Si: 228.1334; found: 228.1333.

41
- 0001759867
- For the known synthetic methods of silole, silaindene derivatives, see: a
- For the known synthetic methods of silole, silaindene derivatives, see: (a) Dubac, J.; Laporterie, A.; Manuel, G. Chem. Rev. 1990, 90, 215.
- (1990) Chem. Rev , vol.90 , pp. 215
- Dubac, J.¹ Laporterie, A.² Manuel, G.³

42
- 0026597848
- (b) Märkl, G.; Berr, K.-P. Tetrahedron Lett. 1992, 33, 1601.
- (1992) Tetrahedron Lett , vol.33 , pp. 1601
- Märkl, G.¹ Berr, K.-P.²

43
- 0001222316
- (c) Tamao, K.; Yamaguchi, S.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 11715.
- (1994) J. Am. Chem. Soc , vol.116 , pp. 11715
- Tamao, K.¹ Yamaguchi, S.² Shiro, M.³

44
- 0000974285
- (d) Fagan, P. J.; Nugent, W. A.; Calabrese, J. C. J. Am. Chem. Soc. 1994, 116, 1880.
- (1994) J. Am. Chem. Soc , vol.116 , pp. 1880
- Fagan, P.J.¹ Nugent, W.A.² Calabrese, J.C.³

45
- 0034731628
- (e) Sudo, T.; Asao, N.; Yamamoto, Y. J. Org. Chem. 2000, 65, 8919.
- (2000) J. Org. Chem , vol.65 , pp. 8919
- Sudo, T.¹ Asao, N.² Yamamoto, Y.³

46
- 11144347642
- (f) Wang, Z.; Fang, H.; Xi, Z. Tetrahedron Lett. 2005, 46, 499.
- (2005) Tetrahedron Lett , vol.46 , pp. 499
- Wang, Z.¹ Fang, H.² Xi, Z.³

47
- 27644463924
- (g) Yamaguchi, S.; Xu, C.; Yamada, H.; Wakamiya, A. J. Organomet. Chem. 2005, 690, 5365.
- (2005) J. Organomet. Chem , vol.690 , pp. 5365
- Yamaguchi, S.¹ Xu, C.² Yamada, H.³ Wakamiya, A.⁴

48
- 32544448193
- (h) Hudrlik, P. F.; Dai, D.; Hudrlik, A. M. J. Organomet. Chem. 2006, 691, 1257.
- (2006) J. Organomet. Chem , vol.691 , pp. 1257
- Hudrlik, P.F.¹ Dai, D.² Hudrlik, A.M.³

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