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Journal of the American Chemical Society

Volumn 130, Issue 5, 2008, Pages 1526-1527

Silylboranes bearing dialkylamino groups on silicon as silylene equivalents: Palladium-catalyzed regioselective synthesis of 2,4-disubstituted siloles

(3) Ohmura, Toshimichi a Masuda, Kohei a Suginome, Michinori a

a KYOTO UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; BORANE DERIVATIVE; PALLADIUM; RUTHENIUM; SILANE; SILICON; SILOLE DERIVATIVE; SILYLBORANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 38949145300 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja073896h Document Type: Article

Times cited : (70)

References (45)

1
- 0000383676
- Yamaguchi, S.; Tamao, K. Bull. Chem. Soc. Jpn. 1996, 69, 2327.
- (1996) Bull. Chem. Soc. Jpn , vol.69 , pp. 2327
- Yamaguchi, S.¹ Tamao, K.²

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

3
- 0034595330
- (b) Yamaguchi, S.; Endo, T.; Uchida, M.; Izumizawa, T.; Furukawa, K.; Tamao, K. Chem.-Eur. J. 2000, 6, 1683.
- (2000) Chem.-Eur. J , vol.6 , pp. 1683
- Yamaguchi, S.¹ Endo, T.² Uchida, M.³ Izumizawa, T.⁴ Furukawa, K.⁵ Tamao, K.⁶

4
- 17144428147
- (c) Yamaguchi, S.; Tamao, K. Chem. Lett. 2005, 34, 2.
- (2005) Chem. Lett , vol.34 , pp. 2
- Yamaguchi, S.¹ Tamao, K.²

5
- 31344469902
- (d) Yamaguchi, S.; Xu, C. J. Synth. Org. Chem. Jpn. 2005, 63, 1115.
- (2005) J. Synth. Org. Chem. Jpn , vol.63 , pp. 1115
- Yamaguchi, S.¹ Xu, C.²

6
- 33645699748
- (e) Yamaguchi, S.; Xu, C.; Okamoto, T. Pure Appl. Chem. 2006, 78, 721.
- (2006) Pure Appl. Chem , vol.78 , pp. 721
- Yamaguchi, S.¹ Xu, C.² Okamoto, T.³

7
- 38949124377
- For selected reviews, see: a
- For selected reviews, see: (a) Dubac, J.; Laporterie, A.; Manuel, G. Chem. Rev. 1993, 93, 215.
- (1993) Chem. Rev , vol.93 , pp. 215
- Dubac, J.¹ Laporterie, A.² Manuel, G.³

8
- 0036643739
- (b) Yamaguchi, S.; Tamao, K. J. Organomet. Chem. 2002, 653, 223.
- (2002) J. Organomet. Chem , vol.653 , pp. 223
- Yamaguchi, S.¹ Tamao, K.²

9
- 0242352408
- (c) Hissler, M.; Dyer, P. W.; Régis, R. Coord. Chem. Rev. 2003, 244, 1.
- (2003) Coord. Chem. Rev , vol.244 , pp. 1
- Hissler, M.¹ Dyer, P.W.² Régis, R.³

10
- 33646339660
- (d) Wrackmeyer, B. Heteroatom Chem. 2006, 17, 188.
- (2006) Heteroatom Chem , vol.17 , pp. 188
- Wrackmeyer, B.¹

11
- 33846421611
- For recent examples, see: e
- For recent examples, see: (e) 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

12
- 33947429150
- (f) Wang, C.; Luo, Q.; Sun, H.; Guo, X.; Xi, Z. J. Am. Chem. Soc. 2007, 129, 3094.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 3094
- Wang, C.¹ Luo, Q.² Sun, H.³ Guo, X.⁴ Xi, Z.⁵

13
- 0001317878
- (a) Okinoshima, H.; Yamamoto, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 9263.
- (1972) J. Am. Chem. Soc , vol.94 , pp. 9263
- Okinoshima, H.¹ Yamamoto, K.² Kumada, M.³

14
- 0002709608
- (b) Okinoshima, H.; Yamamoto, K.; Kumada, M. J. Organomet. Chem. 1975, 86, C27.
- (1975) J. Organomet. Chem , vol.86
- Okinoshima, H.¹ Yamamoto, K.² Kumada, M.³

15
- 0000731937
- (c) Tamao, K.; Yamaguchi, S.; Shiozaki, M.; Nakagawa, Y.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 5867.
- (1992) J. Am. Chem. Soc , vol.114 , pp. 5867
- Tamao, K.¹ Yamaguchi, S.² Shiozaki, M.³ Nakagawa, Y.⁴ Ito, Y.⁵

16
- 0001146448
- Ishikawa, M.; Matsuzawa, S.; Hirotsu, K.; Kamitori, S.; Higuchi, T. Organometallics 1984, 3, 1930.
- (1984) Organometallics , vol.3 , pp. 1930
- Ishikawa, M.¹ Matsuzawa, S.² Hirotsu, K.³ Kamitori, S.⁴ Higuchi, T.⁵

17
- 0001412528
- Schäfer, A.; Weidenbruch, M.; Pohl, S. J. Organomet. Chem. 1985, 282, 305.
- (1985) J. Organomet. Chem , vol.282 , pp. 305
- Schäfer, A.¹ Weidenbruch, M.² Pohl, S.³

18
- 0000835743
- Ikenaga, K.; Hiramatsu, K.; Nasaka, N.; Matsumoto, S. J. Org. Chem. 1993, 58, 5045.
- (1993) J. Org. Chem , vol.58 , pp. 5045
- Ikenaga, K.¹ Hiramatsu, K.² Nasaka, N.³ Matsumoto, S.⁴

19
- 85022518538
- (a) Sakurai, H.; Kamiyama, Y.; Nakadaira, Y. J. Am. Chem. Soc. 1977, 99, 3879.
- (1977) J. Am. Chem. Soc , vol.99 , pp. 3879
- Sakurai, H.¹ Kamiyama, Y.² Nakadaira, Y.³

20
- 0002149628
- (b) Seyferth, D.; Duncan, D. P.; Vick, S. C. J. Organomet. Chem. 1977, 125, C5.
- (1977) J. Organomet. Chem , vol.125
- Seyferth, D.¹ Duncan, D.P.² Vick, S.C.³

21
- 0001898048
- (c) Seyferth, D.; Vick, S. C.; Shannon, M. L.; Lim, T. F. O.; Duncan, D. P. J. Organomet. Chem. 1977, 135, C37.
- (1977) J. Organomet. Chem , vol.135
- Seyferth, D.¹ Vick, S.C.² Shannon, M.L.³ Lim, T.F.O.⁴ Duncan, D.P.⁵

22
- 0002588729
- (d) Ishikawa, M.; Sugisawa, H.; Harata, O.; Kumada, M. J. Organomet. Chem. 1981, 217, 43.
- (1981) J. Organomet. Chem , vol.217 , pp. 43
- Ishikawa, M.¹ Sugisawa, H.² Harata, O.³ Kumada, M.⁴

23
- 33845471396
- (e) Seyferth, D.; Vick, S. C.; Shannon, M. L. Organometallics 1984, 3, 1897.
- (1984) Organometallics , vol.3 , pp. 1897
- Seyferth, D.¹ Vick, S.C.² Shannon, M.L.³

24
- 0002511383
- (f) Seyferth, D.; Shannon, M. L.; Vick, S. C.; Lim, T. F. O. Organometallics 1985, 4, 57.
- (1985) Organometallics , vol.4 , pp. 57
- Seyferth, D.¹ Shannon, M.L.² Vick, S.C.³ Lim, T.F.O.⁴

25
- 0001193942
- (g) Ishikawa, M.; Matsuzawa, S.; Higuchi, T.; Kamitori, S.; Hirotsu, K. Organometallics 1985, 4, 2040.
- (1985) Organometallics , vol.4 , pp. 2040
- Ishikawa, M.¹ Matsuzawa, S.² Higuchi, T.³ Kamitori, S.⁴ Hirotsu, K.⁵

26
- 0027514961
- (h) Belzner, J.; Ihmels, H. Tetrahedron Lett. 1993, 34, 6541.
- (1993) Tetrahedron Lett , vol.34 , pp. 6541
- Belzner, J.¹ Ihmels, H.²

27
- 0000999374
- (i) Palmer, W. S.; Woerpel, K. A. Organometallics 1997, 16, 4824.
- (1997) Organometallics , vol.16 , pp. 4824
- Palmer, W.S.¹ Woerpel, K.A.²

28
- 0001681267
- (a) Palmer, W. S.; Woerpel, K. A. Organometallics 1997, 16, 1097.
- (1997) Organometallics , vol.16 , pp. 1097
- Palmer, W.S.¹ Woerpel, K.A.²

29
- 0035921544
- (b) Palmer, W. S.; Woerpel, K. A. Organometallics 2001, 20, 3691.
- (2001) Organometallics , vol.20 , pp. 3691
- Palmer, W.S.¹ Woerpel, K.A.²

30
- 33745518364
- For recent examples, see: a
- For recent examples, see: (a) Ohmura, T.; Suginome, M. Org. Lett. 2006, 8, 2503.
- (2006) Org. Lett , vol.8 , pp. 2503
- Ohmura, T.¹ Suginome, M.²

31
- 33750053862
- (b) Ohmura, T.; Furukawa, H.; Suginome, M. J. Am. Chem. Soc. 2006, 128, 13366.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 13366
- Ohmura, T.¹ Furukawa, H.² Suginome, M.³

32
- 33750350817
- (c) Ohmura, T.; Taniguchi, H.; Suginome, M. J. Am. Chem. Soc. 2006, 128, 13682.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 13682
- Ohmura, T.¹ Taniguchi, H.² Suginome, M.³

33
- 33947645264
- (d) Ohmura, T.; Taniguchi, H.; Kondo, Y.; Suginome, M. J. Am. Chem. Soc. 2007, 129, 3518.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 3518
- Ohmura, T.¹ Taniguchi, H.² Kondo, Y.³ Suginome, M.⁴

34
- 0041888254
- For recent reviews, see: e
- For recent reviews, see: (e) Suginome, M.; Ito, Y. J. Organomet. Chem. 2003, 680, 43.
- (2003) J. Organomet. Chem , vol.680 , pp. 43
- Suginome, M.¹ Ito, Y.²

35
- 33745712700
- (f) Beletskaya, I.; Moberg, C. Chem. Rev. 2006, 106, 2320.
- (2006) Chem. Rev , vol.106 , pp. 2320
- Beletskaya, I.¹ Moberg, C.²

36
- 84906432766
- Suginome, M.; Matsuda, T.; Ohmura, T.; Seki, A.; Murakami, M. In Comprehensive Organometallic Chemistry III; Crabtree, R. H., Mingos, D. M. P., Eds.: Ojima, I., Ed.; Elsevier: Oxford, 2007; 10, p 725.
- (g) Suginome, M.; Matsuda, T.; Ohmura, T.; Seki, A.; Murakami, M. In Comprehensive Organometallic Chemistry III; Crabtree, R. H., Mingos, D. M. P., Eds.: Ojima, I., Vol. Ed.; Elsevier: Oxford, 2007; Vol. 10, p 725.

37
- 33947140299
- Ohmura, T.; Masuda, K.; Furukawa, H.; Suginome, M. Organometallics 2007, 26, 1291.
- (2007) Organometallics , vol.26 , pp. 1291
- Ohmura, T.¹ Masuda, K.² Furukawa, H.³ Suginome, M.⁴

38
- 34547151955
- Wrackmeyer, B.; Kehr, G.; Süss, J. Chem. Ber. 1993, 126, 2221. See also refs 6 and 8h.
- Wrackmeyer, B.; Kehr, G.; Süss, J. Chem. Ber. 1993, 126, 2221. See also refs 6 and 8h.

39
- 0042192126
- Suginome, M.; Ohmura, T.; Miyake, Y.; Mitani, S.; Ito, Y.; Murakami, M. J. Am. Chem. Soc. 2003, 125, 11174.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 11174
- Suginome, M.¹ Ohmura, T.² Miyake, Y.³ Mitani, S.⁴ Ito, Y.⁵ Murakami, M.⁶

40
- 38949125805
- In the absence of alkyne, silylborane 4a slowly reacted at room temperature in the presence of the Pd/PPh3 complex (10 mol , resulting in the formation of 11a (84% yield after 48 h) with organosilicon compounds, which exhibited 1H NMR signals in the region of -1.0 to 0.6 ppm. Although they were hardly identifiable, dodecamethylcyclohexasilane was detected by 1H NMR and GCMS analysis as a very minor <1, component
- 1H NMR and GCMS analysis as a very minor (<1%) component.

41
- 38949125079
- 2(2-biphenyl)].
- 2(2-biphenyl)].

42
- 38949113666
- 2.
- 2.

43
- 0037024173
- Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 6343
- Littke, A.F.¹ Schwarz, L.² Fu, G.C.³

44
- 38949102639
- 10e: UV/vis λmax 338 nm (ε 2.0 × 103, FL λmax 452 nm, Φf 0.13. 17a: UV/vis λmax 403 nm (ε 2.5 × 10 3, FL λmax 456 nm, Φf, 0.069. 17b: UV/vis λmax 420 nm (ε 2.2 × 10 4, FL λmax 516 nm, Φf, 0.015. The photophysical data were measured in CHCl3. Quantum yields (Φf) were determined with reference to quinine sulfate in 0.1 M H2SO4 excited at 366 nm
- 4 (excited at 366 nm).

45
- 34249011440
- Ueno, S.; Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2007, 129, 6098.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 6098
- Ueno, S.¹ Chatani, N.² Kakiuchi, F.³

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