SCOPUS 정보 검색 플랫폼

Organometallics

Volumn 27, Issue 15, 2008, Pages 3635-3638

Acid-promoted hydrogen migration in (2-allylphenoxo)ruthenium(II) to form an η3-allyl complex

(6) Hirano, Masafumi a Kuga, Toshinori a Kitamura, Mariko a Kanaya, Susumu a Komine, Nobuyuki a Komiya, Sanshiro a

a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN MIGRATION; RUTHENIUM;

ACIDS;

EID: 50549097290 PISSN: 02767333 EISSN: None Source Type: Journal
DOI: 10.1021/om800318z Document Type: Article

Times cited : (8)

References (45)

1
- 0003818424
- Reidel: Dordrecht, The Netherlands
- (a) Shilov, A. E. The Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reidel: Dordrecht, The Netherlands, 1984.
- (1984) The Activation of Saturated Hydrocarbons by Transition Metal Complexes
- Shilov, A.E.¹

2
- 17344362973
- (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245.
- (1985) Chem. Rev , vol.85 , pp. 245
- Crabtree, R.H.¹

3
- 0000313458
- (c) Wasserman, E. P.; Moore, C. B.; Bergman, R. G. Science 1992, 255, 315.
- (1992) Science , vol.255 , pp. 315
- Wasserman, E.P.¹ Moore, C.B.² Bergman, R.G.³

4
- 50549087730
- Homogeneous Transition Metal Catalyzed Reactions; Moser, W. R.; Slocum, D. W., Eds.; Advances in Chemistry 230; American Chemical Society: Washington, D.C., 1992.
- (d) Homogeneous Transition Metal Catalyzed Reactions; Moser, W. R.; Slocum, D. W., Eds.; Advances in Chemistry 230; American Chemical Society: Washington, D.C., 1992.

5
- 0000820085
- (e) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Påeterson, T. H. Acc. Chem. Res. 1995, 28, 154.
- (1995) Acc. Chem. Res , vol.28 , pp. 154
- Arndtsen, B.A.¹ Bergman, R.G.² Mobley, T.A.³ Påeterson, T.H.⁴

6
- 0000826001
- (a) Hirano, M.; Kurata, N.; Marumo, T.; Komiya, S. Organometallics 1998, 17, 501.
- (1998) Organometallics , vol.17 , pp. 501
- Hirano, M.¹ Kurata, N.² Marumo, T.³ Komiya, S.⁴

7
- 0002733993
- (b) Hirano, M.; Kurata, N.; Komiya, S. J. Organomet. Chem. 2000, 607, 18.
- (2000) J. Organomet. Chem , vol.607 , pp. 18
- Hirano, M.¹ Kurata, N.² Komiya, S.³

8
- 26444533387
- (c) Hirano, M.; Sakaguchi, Y.; Yajima, T.; Kurata, N.; Komine, N.; Komiya, S. Organometallics 2005, 24, 4799.
- (2005) Organometallics , vol.24 , pp. 4799
- Hirano, M.¹ Sakaguchi, Y.² Yajima, T.³ Kurata, N.⁴ Komine, N.⁵ Komiya, S.⁶

9
- 34247527853
- (d) Hirano, M.; Sato, H.; Kurata, N.; Komine, N.; Komiya, S. Organometallics 2007, 26, 2005.
- (2005) Organometallics , vol.2007 , pp. 26
- Hirano, M.¹ Sato, H.² Kurata, N.³ Komine, N.⁴ Komiya, S.⁵

10
- 0000829601
- Bryndza, H. E.; Domaille, P. J.; Paciello, R. A.; Bercaw, J. E. Organometallics 1989, 8, 379.
- (1989) Organometallics , vol.8 , pp. 379
- Bryndza, H.E.¹ Domaille, P.J.² Paciello, R.A.³ Bercaw, J.E.⁴

11
- 33745356338
- Feng, Y.; Lail, M.; Foley, N. A.; Gunnoe, T. B.; Barakat, K. A.; Cunddari, T. R.; Petersen, J. L. J. Am. Chem. Soc. 2006, 128, 7982.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 7982
- Feng, Y.¹ Lail, M.² Foley, N.A.³ Gunnoe, T.B.⁴ Barakat, K.A.⁵ Cunddari, T.R.⁶ Petersen, J.L.⁷

12
- 34250753770
- and references cited therein
- Gunnoe, T. B. Eur. J. Inorg. Chem. 2007, 1185, and references cited therein.
- (2007) Eur. J. Inorg. Chem , pp. 1185
- Gunnoe, T.B.¹

13
- 0000461987
- Reviews of monomeric alkoxo and aryloxoruthenium complexes: a
- Reviews of monomeric alkoxo and aryloxoruthenium complexes: (a) Bergman, R. G. Polyhedron 1995, 14, 3227.
- (1995) Polyhedron , vol.14 , pp. 3227
- Bergman, R.G.¹

14
- 0010886102
- Abel, W, Stone, F. G. A, Wilkinson, G, Eds, Pergamon: Oxford, U.K, Chapter 8, p
- (b) Bennett, M. A.; Khan, K.; Wenger, E. In Comprehensive Organometallic Chemistry II; Abel, W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 7, Chapter 8, p 490.
- (1995) Comprehensive Organometallic Chemistry II , vol.7 , pp. 490
- Bennett, M.A.¹ Khan, K.² Wenger, E.³

15
- 50549102614
- 2. This reaction will be reported elsewhere.
- 2. This reaction will be reported elsewhere.

16
- 50549101768
- As a typical example, the characterization of 2c is described. 2c: 1H NMR (300 MHz, C6D6, 30.0 °C) δ 3.03 (d, 3JH-H, 6.9 Hz, 2H, benzylic CH2, 4.21 (s, 5H, Cp, 5.04 (d, 3J H-H, 9.9 Hz, 1H, CH2, 5.06 (d, 3J H-H, 16.5 Hz, 1H, CH2, 6.11 (ddt, 3JH-H, 16.5, 3JH-H, 9.9, 3J H-H, 6.9 Hz, 1H, CH, 7.6 (m, 6H, PPh3, other aromatic resonances obscured by other aromatic protons in 3c and free PPh3. 31P{1H} NMR (122 MHz, C 6D6, δ 40.4 (s, Complex 2c constitutes an equilibrium mixture with the monophosphine complex 3c, having a π coordination of the alkenyl group in benzene-d6 solution (see ref 11, IR (KBr, cm-1, 3051 m
- 2Ru: C, 72.89; H, 5.38. Found: C, 72.93; H, 5.14.

17
- 0001281176
- Bruce, M. I.; Humphrey, M. G.; Swincer, A. G.; Wallis, R. C. Aust. J. Chem. 1984, 37, 1747.
- (1984) Aust. J. Chem , vol.37 , pp. 1747
- Bruce, M.I.¹ Humphrey, M.G.² Swincer, A.G.³ Wallis, R.C.⁴

18
- 50549083645
- w) = 0.0483 (0.0599) and GOF = 1.101.
- w) = 0.0483 (0.0599) and GOF = 1.101.

19
- 50549100920
- 3c: 1H NMR (300 MHz, C6D6, 18.0°C) δ 1.84 (dd, 2JH-H, 12.0, 3JH-H, 11.7 Hz, 1H, benzylic CHH, 2.78 (dd, 3JH-H, 13.8, 3JH-P, 10.8 Hz, 1H, CH2, 3.14 (br dd, 2JH-H, 12, 3JH-H, 4 Hz, 1H, benzylic CHH, 3.20 (d, 3JH-H, 7.8 Hz, 1H, CH2, 3.96 (s, 5H, Cp, 5.59 (m, 1H, CH, 6.81 (td, 3JH-H, 7.5, 4JH-H, 1.2 Hz, 1H, 4-C6H4, 6.9 (br m, 1H, C6H4, 7.0 (m, 9H, m- and p-PPh 3, 7.26 (t, 3JH-H, 8 Hz, 2H, C 6H4, 7.8 (m, 6H, o-PPh3, 31P( 1H) NMR (122 MHz, C6D6) δ 48.97 s
- 6) δ 48.97 (s).

20
- 50549101275
- 4c: 1H NMR (300 MHz, C6D6) δ 1.01 (ddd, 3JH-P, 16, 3J H-H, 10, 2JH-H, 1 Hz, 1H, anti-CHH, 1.86 (dd, 3JH-H, 10, 3J H-P, 2 Hz, 1H, CHAr, 2.97 (dd, 3JH-H, 7, 2JH-H, 2 Hz, 1H a syn-CHH, 4.12 (s, 5H, Cp, 4.62 (tdd, 3JH-H, 10, 3JH-H, 7, 3JH-P, 1 Hz, 1H, central-CH, 6.80 (td, 3JH-H, 7, 4JH-H, 1 Hz, 1H, 4-C6H4, 7.01 (m, 10H, m- and p-PPh3, 7.16 (overlapped with signal due to residual signal of deuterated benzene, C6H4, 7.40 (d, 3JH-H, 8 Hz, 1H, 6-C6H4, 7.71 t, 3JH-H, 10 Hz, 6H
- 29OPRu: C, 68.44; H, 5.20. Found: C, 68.62; H, 5.98.

21
- 50549099546
- w) = 0.0305 (0.0485) and GOF = 1.244.
- w) = 0.0305 (0.0485) and GOF = 1.244.

22
- 14544272753
- Bi, S.; Ariafard, A.; Jia, G.; Lin, Z. Organometallics 2005, 24, 680.
- (2005) Organometallics , vol.24 , pp. 680
- Bi, S.¹ Ariafard, A.² Jia, G.³ Lin, Z.⁴

23
- 0002709321
- Stradins, J.; Hasanli, B. J. Electroanal. Chem. Interfacial Electrochem. 1993, 353, 57.
- (1993) Electroanal. Chem. Interfacial Electrochem , vol.353 , pp. 57
- Stradins, J.¹ Hasanli, B.J.²

24
- 50549091672
- 6 at 20 °C: δ 1.98 (0.02 M of 2-allylphenol), δ 2.1 (0.04 M of 2-allylphenol), δ 2.18 (0.06 M of 2-allylphenol), δ 2.28 (0.10 M of 2-allylphenol), δ 2.43 (0.20 M of 2-allylphenol) (cf. methylene resonence in 3c: δ 1.84).
- 6 at 20 °C: δ 1.98 (0.02 M of 2-allylphenol), δ 2.1 (0.04 M of 2-allylphenol), δ 2.18 (0.06 M of 2-allylphenol), δ 2.28 (0.10 M of 2-allylphenol), δ 2.43 (0.20 M of 2-allylphenol) (cf. methylene resonence in 3c: δ 1.84).

25
- 50549104252
- 6 at 20 °C: δ 5.52 at 0.02 M, δ 5.05 at 0.10 M, δ 4.73 at 0.20 M in the presence of 2c/3c (0.02 M) (cf. free 2-allylphenol: δ 4.43).
- 6 at 20 °C: δ 5.52 at 0.02 M, δ 5.05 at 0.10 M, δ 4.73 at 0.20 M in the presence of 2c/3c (0.02 M) (cf. free 2-allylphenol: δ 4.43).

26
- 0001238794
- Bickford, C. C.; Johnson, T. J.; Davidson, E. R.; Caulton, K. G. Inorg. Chem. 1994, 33, 1080.
- (1994) Inorg. Chem , vol.33 , pp. 1080
- Bickford, C.C.¹ Johnson, T.J.² Davidson, E.R.³ Caulton, K.G.⁴

27
- 50549099992
- (a) Yong-Joo, K.; Jae-Young, L.; Osakada, K. J. Organomet. Chem. 1998, 558, 41.
- (1998) J. Organomet. Chem , vol.558 , pp. 41
- Yong-Joo, K.¹ Jae-Young, L.² Osakada, K.³

28
- 37049080559
- (b) Komiya, S.; Iwata, M.; Sone, T.; Fukuoka, A. J. Chem. Soc., Chem. Commun. 1992, 1109.
- (1992) J. Chem. Soc., Chem. Commun , pp. 1109
- Komiya, S.¹ Iwata, M.² Sone, T.³ Fukuoka, A.⁴

29
- 0000763430
- (c) Simpson, R. D.; Bergman, R. G. Organometallics 1992, 11, 4306.
- (1992) Organometallics , vol.11 , pp. 4306
- Simpson, R.D.¹ Bergman, R.G.²

30
- 33751499127
- (d) Osakada, K.; Ohshiro, K.; Yamamoto, A. Organometallics 1991, 10, 404.
- (1991) Organometallics , vol.10 , pp. 404
- Osakada, K.¹ Ohshiro, K.² Yamamoto, A.³

31
- 0000698281
- (e) Osakada, K.; Kim, Y.; Tanaka, M.; Ishiguro, S.; Yamamoto, A. Inorg. Chem. 1991, 30, 197.
- (1991) Inorg. Chem , vol.30 , pp. 197
- Osakada, K.¹ Kim, Y.² Tanaka, M.³ Ishiguro, S.⁴ Yamamoto, A.⁵

32
- 0025248621
- (f) Kim, Y.; Osakada, K.; Takenaka, A.; Yamamoto, A. J. Am. Chem. Soc. 1990, 112, 1096.
- (1990) Am. Chem. Soc , vol.112 , pp. 1096
- Kim, Y.¹ Osakada, K.² Takenaka, A.³ Yamamoto, A.J.⁴

33
- 0001731603
- (g) Osakada, K.; Kim, Y.; Yamamoto, A. J. Organomet. Chem. 1990, 382, 303.
- (1990) Organomet. Chem , vol.382 , pp. 303
- Osakada, K.¹ Kim, Y.² Yamamoto, A.J.³

34
- 33845281813
- (h) Kegley, S. E.; Schaverien, C. J.; Freudenberger, J. H.; Bergman, R. G.; Nolan, S. P.; Hoff, C. D. J. Am. Chem. Soc. 1987, 109, 6563.
- (1987) J. Am. Chem. Soc , vol.109 , pp. 6563
- Kegley, S.E.¹ Schaverien, C.J.² Freudenberger, J.H.³ Bergman, R.G.⁴ Nolan, S.P.⁵ Hoff, C.D.⁶

35
- 50549087257
- Although 2c · HX could not be observed, it is reasonable to propose analogous hydrogen bonding under acidic conditions to give 4c. However, we believe that this process is not a major process, because preliminary results show that treatment of the DPPE analogue of 2c, RuCp(OC6H4CH2CH=CH2)(dppe, with 2-allylphenol did not produce the corresponding η3-allyl complex at all under these conditions. Moreover, the estimated value for k P2 is almost 0 M-1 s-1 see the Supporting Information, However, since we cannot exclude the formation process via 2c · HX completely, such a possibility is also depicted in Scheme 2
- -1 (see the Supporting Information). However, since we cannot exclude the formation process via 2c · HX completely, such a possibility is also depicted in Scheme 2.

36
- 50549095151
- -1 (THF). Conditions: initial concentration of 2c/3c 0.0012 M, 2-allylphenol 250 equiv, temperature 30°C.
- -1 (THF). Conditions: initial concentration of 2c/3c 0.0012 M, 2-allylphenol 250 equiv, temperature 30°C.

37
- 34250753770
- (a) Gunnoe, T. B. Eur. J. Inorg. Chem. 2007, 1185.
- (2007) Eur. J. Inorg. Chem , pp. 1185
- Gunnoe, T.B.¹

38
- 33751436579
- (b) Feng, Y.; Gunnoe, T. B.; Grimes, T. V.; Cundan, T. R. Organometallics 2006, 25, 5456.
- (2006) Organometallics , vol.25 , pp. 5456
- Feng, Y.¹ Gunnoe, T.B.² Grimes, T.V.³ Cundan, T.R.⁴

39
- 33745356338
- (c) Feng, Y.; Lail, M.; Foley, N. A.; Gunnoe, T. B.; Barakat, K. A.; Cundari, T. R.; Petersen, J. L. J. Am. Chem. Soc. 2006, 128, 7982.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 7982
- Feng, Y.¹ Lail, M.² Foley, N.A.³ Gunnoe, T.B.⁴ Barakat, K.A.⁵ Cundari, T.R.⁶ Petersen, J.L.⁷

40
- 26844537380
- (d) Feng, Y.: Lail, M.; Barakat, K. A.; Cundari, T. R.; Gunnoe, T. B.; Petersen, J. L. J. Am. Chem. Soc. 2005, 127, 14174.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 14174
- Feng, Y.¹ Lail, M.² Barakat, K.A.³ Cundari, T.R.⁴ Gunnoe, T.B.⁵ Petersen, J.L.⁶

41
- 34047247918
- (a) Oxgaard, J.; Tenn, W. J., III; Nielsen, R. J.; Periana, R. A.; Goddard, W. A., III Organometallics 2007, 26, 1565.
- (2007) Organometallics , vol.26 , pp. 1565
- Oxgaard, J.¹ Tenn III, W.J.² Nielsen, R.J.³ Periana, R.A.⁴ Goddard III, W.A.⁵

42
- 33750300012
- (b) Tenn, W. J., III; Young, K. J. H.; Oxgaard, J.; Nielsen, R. J.; Goddard, W. A., III; Periana, R. A. Organometallics 2006, 25, 5173.
- (2006) Organometallics , vol.25 , pp. 5173
- Tenn III, W.J.¹ Young, K.J.H.² Oxgaard, J.³ Nielsen, R.J.⁴ Goddard III, W.A.⁵ Periana, R.A.⁶

43
- 26844535480
- Tenn, W. J., III; Young, K. J. H.; Bhalla, G.; Oxgaard, J.; Goddard, W. A., III; Periana, R. A. J. Am. Chem. Soc. 2005, 127, 14172.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 14172
- Tenn III, W.J.¹ Young, K.J.H.² Bhalla, G.³ Oxgaard, J.⁴ Goddard III, W.A.⁵ Periana, R.A.⁶

44
- 14544308809
- In this reference, putative (alkoxo, and (aryloxo)ruthenium(II) complexes were reported to cause an intramolecular C-H bond cleavage reaction
- Koike, T.; Ikariya, T. Organometallics 2005, 24, 724 In this reference, putative (alkoxo)- and (aryloxo)ruthenium(II) complexes were reported to cause an intramolecular C-H bond cleavage reaction.
- (2005) Organometallics , vol.24 , pp. 724
- Koike, T.¹ Ikariya, T.²

45
- 33645463249
- Davies, D. L.; Donald, S. M. A.; Al-Duaij, O.; Macgregor, S. A.; Pölleth, M. J. Am. Chem. Soc. 2006, 128, 4210.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 4210
- Davies, D.L.¹ Donald, S.M.A.² Al-Duaij, O.³ Macgregor, S.A.⁴ Pölleth, M.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.