SCOPUS 정보 검색 플랫폼

Volumn , Issue 17, 2008, Pages 2663-2666

Phosphine-dependent selective cross-dimerization between terminal alkylacetylene and silylacetylene by iridium(I) guanidinate complex-phosphine system

(5) Ogata, Kenichi a Oka, Oji b Toyota, Akinori b Suzuki, Noriyuki c Fukuzawa, Shin Ichi a

a CHUO UNIVERSITY (Japan)

b TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY (Japan)

c RIKEN (Japan)

Author keywords

Alkynes; Coupling; Dimerizations; Enynes; Iridium

Indexed keywords

ACETYLENE DERIVATIVE; ALKYLACETYLENE; ARYLACETYLENE; GUANIDINATE; GUANIDINE DERIVATIVE; IRIDIUM; PHOSPHINE; SILYLACETYLENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIMERIZATION;

EID: 55549093142 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1083514 Document Type: Article

Times cited : (35)

References (43)

1
- 0000501827
- For recent example of transition-metal-catalyzed homodimerization of alkynes, see: a
- For recent example of transition-metal-catalyzed homodimerization of alkynes, see: (a) Ohmura, T.; Yorozuya, S.; Yamamoto, Y.; Miyaura, N. Organometallics 2000, 19, 365.
- (2000) Organometallics , vol.19 , pp. 365
- Ohmura, T.¹ Yorozuya, S.² Yamamoto, Y.³ Miyaura, N.⁴

2
- 0037169069
- (b) Yang, C.; Nolan, S. P. J. Org. Chem. 2002, 67, 591.
- (2002) J. Org. Chem , vol.67 , pp. 591
- Yang, C.¹ Nolan, S.P.²

3
- 0036774953
- (c) Melis, K.; Vos, D. D.; Jacobs, P.; Verpoort, F. J. Organomet. Chem. 2002, 659, 159.
- (2002) J. Organomet. Chem , vol.659 , pp. 159
- Melis, K.¹ Vos, D.D.² Jacobs, P.³ Verpoort, F.⁴

4
- 11144300921
- (d) Ogoshi, S.; Ueta, M.; Oka, M.; Kurosawa, H. Chem. Commun. 2004, 2732.
- (2004) Chem. Commun , pp. 2732
- Ogoshi, S.¹ Ueta, M.² Oka, M.³ Kurosawa, H.⁴

5
- 24944453067
- (e) Chen, X.; Xue, P.; Sung, H. H. Y.; Williams, I. D.; Peruzzini, M.; Bianchini, C.; Jia, G. Organometallics 2005, 24, 4330.
- (2005) Organometallics , vol.24 , pp. 4330
- Chen, X.¹ Xue, P.² Sung, H.H.Y.³ Williams, I.D.⁴ Peruzzini, M.⁵ Bianchini, C.⁶ Jia, G.⁷

6
- 12344324618
- (f) Lee, C.-C.; Lin, Y.-C.; Liu, Y.-H.; Wang, Y. Organometallics 2005, 24, 136.
- (2005) Organometallics , vol.24 , pp. 136
- Lee, C.-C.¹ Lin, Y.-C.² Liu, Y.-H.³ Wang, Y.⁴

7
- 33645452006
- (g) Weng, W.; Guo, C.; Celenligil-Cetin, R.; Foxman, B. M.; Ozerov, O. V. Chem. Commun. 2006, 197.
- (2006) Chem. Commun , pp. 197
- Weng, W.¹ Guo, C.² Celenligil-Cetin, R.³ Foxman, B.M.⁴ Ozerov, O.V.⁵

8
- 0001353019
- (a) Trost, B. M.; McIntoshi, M. C. J. Am. Chem. Soc. 1995, 117, 7255.
- (1995) J. Am. Chem. Soc , vol.117 , pp. 7255
- Trost, B.M.¹ McIntoshi, M.C.²

9
- 0031046817
- (b) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rhter, G. J. Am. Chem. Soc. 1997, 119, 698.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 698
- Trost, B.M.¹ Sorum, M.T.² Chan, C.³ Harms, A.E.⁴ Rhter, G.⁵

10
- 0001344076
- (c) Yi, C. S.; Liu, N. Organometallics 1998, 17, 3158.
- (1998) Organometallics , vol.17 , pp. 3158
- Yi, C.S.¹ Liu, N.²

11
- 0034730992
- (d) Trost, B. M.; Frontier, A. J. J. Am. Chem. Soc. 2000, 122, 11727.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 11727
- Trost, B.M.¹ Frontier, A.J.²

12
- 1542268871
- (e) Chen, L.; Li, C. Tetrahedron Lett. 2004, 45, 2771.
- (2004) Tetrahedron Lett , vol.45 , pp. 2771
- Chen, L.¹ Li, C.²

13
- 20044373868
- (f) Hirabayashi, T.; Sakaguchi, S.; Ishii, Y. Adv. Synth. Catal. 2005, 347, 872.
- (2005) Adv. Synth. Catal , vol.347 , pp. 872
- Hirabayashi, T.¹ Sakaguchi, S.² Ishii, Y.³

14
- 37349118689
- (g) Nishimura, T.; Guo, X.-X.; Ohnishi, K.; Hayashi, T. Adv. Synth. Catal. 2007, 349, 2669.
- (2007) Adv. Synth. Catal , vol.349 , pp. 2669
- Nishimura, T.¹ Guo, X.-X.² Ohnishi, K.³ Hayashi, T.⁴

15
- 34547184427
- (h) Katagiri, T.; Tsurugi, H.; Funayama, A.; Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 830.
- (2007) Chem. Lett , vol.36 , pp. 830
- Katagiri, T.¹ Tsurugi, H.² Funayama, A.³ Satoh, T.⁴ Miura, M.⁵

16
- 0001571404
- (a) Akita, M.; Yasuda, H.; Nakamura, A. Bull. Chem. Soc. Jpn. 1984, 57, 480.
- (1984) Bull. Chem. Soc. Jpn , vol.57 , pp. 480
- Akita, M.¹ Yasuda, H.² Nakamura, A.³

17
- 1842473945
- (b) Wang, J.; Kapon, M.; Berthet, J. C.; Ephritikhine, M.; Eisen, M. S. Inorg. Chim. Acta 2002, 334, 183.
- (2002) Inorg. Chim. Acta , vol.334 , pp. 183
- Wang, J.¹ Kapon, M.² Berthet, J.C.³ Ephritikhine, M.⁴ Eisen, M.S.⁵

18
- 25144435810
- (c) Katayama, H.; Yari, H.; Tanaka, M.; Ozawa, F. Chem. Commun. 2005, 4336.
- (2005) Chem. Commun , pp. 4336
- Katayama, H.¹ Yari, H.² Tanaka, M.³ Ozawa, F.⁴

19
- 47549116389
- (d) Katagiri, T.; Tsurugi, H.; Satoh, T.; Miura, M. Chem. Commun. 2008, 3405.
- (2008) Chem. Commun , pp. 3405
- Katagiri, T.¹ Tsurugi, H.² Satoh, T.³ Miura, M.⁴

20
- 34547163896
- (e) Tsukada, N.; Ninomiya, S.; Aoyama, Y.; Inoue, Y. Org. Lett. 2007, 9, 2919.
- (2007) Org. Lett , vol.9 , pp. 2919
- Tsukada, N.¹ Ninomiya, S.² Aoyama, Y.³ Inoue, Y.⁴

21
- 34547745406
- Ogata, K.; Toyota, A. J. Organomet. Chem. 2007, 692, 4139.
- (2007) J. Organomet. Chem , vol.692 , pp. 4139
- Ogata, K.¹ Toyota, A.²

22
- 0035009772
- and references therein
- Baiely, P. J.; Pace, S. Coord. Chem. Rev. 2001, 214, 91; and references therein.
- (2001) Coord. Chem. Rev , vol.214 , pp. 91
- Baiely, P.J.¹ Pace, S.²

23
- 55549143182
- Synthesis of {Ir[(N2 (i-Pr) 2CN(i-Pr)2](cod, 1) A solution of [IrCl(cod)]2 (281 mg, 0.42 mmol) in THF (5 mL) was cooled to -78 °C, and then a THF solution of Li[(N2 (i-Pr) 2CN(Z-Pr)2, which was prepared by the reaction of the DIC (0.13 mL, 0.84 mmol) with LDA solution (1.8 M in heptane-THF-ethylbenzene solution, 0.48 mL, 0.86 mmol) at -78 °C, was added. The mixture was allowed to warm to r.t. After 4 h, the volatiles were removed under reduced pressure. The residual solid was extracted with toluene and the filtrate was evaporated off under high vacuum to give orange complex 1 (278 mg, 0.53 mmol, 63, 1H NMR (400 MHz, C6D6, δ, 0.96 (d, J, 6.4 Hz, 12 H, i-PrCH3, 1.23 (d, J, 6.9 Hz, 12 H, i-PrCH3, 1.39 (d, J, 7.8 Hz, 4 H, cod, 2.20 br, 4 H
- 3: C, 47.88; H, 7.65; N, 7.98. Found: C, 47.82; H, 7.60; N, 8.00.

24
- 4243120159
- (a) Jenke, T.; Stoeckli-Evans, H.; Bodensieck, U.; Suess-Fink, G. J. Organomet. Chem. 1991, 401, 347.
- (1991) J. Organomet. Chem , vol.401 , pp. 347
- Jenke, T.¹ Stoeckli-Evans, H.² Bodensieck, U.³ Suess-Fink, G.⁴

25
- 37049070654
- (b) Yip, H.-K.; Che, C.-M.; Zhou, Z.-Y.; Mak, T. C. W. J. Chem. Soc., Chem. Commun. 1992, 1369.
- (1992) J. Chem. Soc., Chem. Commun , pp. 1369
- Yip, H.-K.¹ Che, C.-M.² Zhou, Z.-Y.³ Mak, T.C.W.⁴

26
- 33748495537
- (c) Bailey, P. J.; Mitchell, L. A.; Parson, S. J. Chem. Soc., Dalton Trans. 1996, 2839.
- (1996) J. Chem. Soc., Dalton Trans , pp. 2839
- Bailey, P.J.¹ Mitchell, L.A.² Parson, S.³

27
- 0001649210
- (d) Dinger, M. B.; Henderson, W. Chem. Commun. 1996, 211.
- (1996) Chem. Commun , pp. 211
- Dinger, M.B.¹ Henderson, W.²

28
- 4544289189
- (e) Holman, K. T.; Robinson, S. D.; Sahajpal, A.; Steed, J. W. J. Chem. Soc., Dalton Trans. 1999, 15.
- (1999) J. Chem. Soc., Dalton Trans , pp. 15
- Holman, K.T.¹ Robinson, S.D.² Sahajpal, A.³ Steed, J.W.⁴

29
- 0034699053
- (f) Foley, S. R.; Yap, G. P. A.; Richeson, D. S. Chem. Commun. 2000, 1515.
- (2000) Chem. Commun , pp. 1515
- Foley, S.R.¹ Yap, G.P.A.² Richeson, D.S.³

30
- 0003015790
- (g) Bailey, P. J.; Grant, K. J.; Mitchell, L. A.; Pace, S.; Parkin, A.; Parsons, S. J. Chem. Soc., Dalton Trans. 2000, 1887.
- (2000) J. Chem. Soc., Dalton Trans , pp. 1887
- Bailey, P.J.¹ Grant, K.J.² Mitchell, L.A.³ Pace, S.⁴ Parkin, A.⁵ Parsons, S.⁶

31
- 33846145569
- (h) Berry, J. F.; Cotton, F. A.; Huang, P.; Murillo, C. A.; Wang, X. Dalton Trans. 2005, 3713.
- (2005) Dalton Trans , pp. 3713
- Berry, J.F.¹ Cotton, F.A.² Huang, P.³ Murillo, C.A.⁴ Wang, X.⁵

32
- 33748661729
- (a) Robinson, S. D.; Sahajal, A. J. Chem. Soc., Dalton Trans. 1997, 3349.
- (1997) J. Chem. Soc., Dalton Trans , pp. 3349
- Robinson, S.D.¹ Sahajal, A.²

33
- 0034732811
- (b) Robinson, S. D.; Sahajpal, A.; Steed, J. Inorg. Chim. Acta 2000, 303, 265.
- (2000) Inorg. Chim. Acta , vol.303 , pp. 265
- Robinson, S.D.¹ Sahajpal, A.² Steed, J.³

34
- 0037036763
- (c) Holland, A. W.; Bergman, R. G. J. Am. Chem. Soc. 2002, 124, 9010.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 9010
- Holland, A.W.¹ Bergman, R.G.²

35
- 55549145631
- int = 0.063), 13318 observed [I > 2σ(I)]. R1 = 0.0353, wR2 = 0.0903 (all data). Atomic coordinates, thermal parameters, bond distances, and angles have been deposited at the Cambridge Crystallographic Data Center. CCDC number: 668977.
- int = 0.063), 13318 observed [I > 2σ(I)]. R1 = 0.0353, wR2 = 0.0903 (all data). Atomic coordinates, thermal parameters, bond distances, and angles have been deposited at the Cambridge Crystallographic Data Center. CCDC number: 668977.

36
- 55549119815
- 2O-hexane (1:3) as eluent. The solvent was removed to give dimeric product 3 or 4.
- 2O-hexane (1:3) as eluent. The solvent was removed to give dimeric product 3 or 4.

37
- 55549131744
- 3P: yield 79%, E/Z = 40:60
- 3P: yield 79%, E/Z = 40:60

38
- 85021622688
- (a) Bianchini, C.; Peruzzini, M.; Zanobini, F.; Frediani, P.; Albinati, A. J. Am. Chem. Soc. 1991, 113, 5453.
- (1991) J. Am. Chem. Soc , vol.113 , pp. 5453
- Bianchini, C.¹ Peruzzini, M.² Zanobini, F.³ Frediani, P.⁴ Albinati, A.⁵

39
- 0001191218
- (b) Wakatsuki, Y.; Yamazaki, H.; Kumegawa, N.; Satoh, T.; Satoh, J. Y. J. Am. Chem. Soc. 1991, 113, 9604.
- (1991) J. Am. Chem. Soc , vol.113 , pp. 9604
- Wakatsuki, Y.¹ Yamazaki, H.² Kumegawa, N.³ Satoh, T.⁴ Satoh, J.Y.⁵

40
- 0000463722
- (c) Bianchini, C.; Frediani, P.; Masi, D.; Peruzzini, M.; Zanobini, F. Organometallics 1994, 13, 4616.
- (1994) Organometallics , vol.13 , pp. 4616
- Bianchini, C.¹ Frediani, P.² Masi, D.³ Peruzzini, M.⁴ Zanobini, F.⁵

41
- 55549148086
- 3): δ = 11.3,

42
- 55549107684
- 1H NMR).
- 1H NMR).

43
- 55549099754
- 2PhP system: yield 88%, E/Z = 9:91.
- 2PhP system: yield 88%, E/Z = 9:91.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.