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Volumn 2, Issue 3, 2005, Pages 219-221

Synthesis of ferrocenylbenzenes via Cp* RuCl-catalyzed partially intramolecular cyclotrimerization of ferrocenylalkynes

Author keywords

Cyclotrimerization; Diyne; Ferrocenylalkyne; Ferrocenylbenzene; Ruthenium catalysis

Indexed keywords


EID: 33645549133     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570178053765258     Document Type: Review
Times cited : (7)

References (21)
  • 16
    • 46249087955 scopus 로고    scopus 로고
    • Typical experimental procedure. Synthesis of 4a: To a solution of Cp*RuC(cod) (3.8 mg, 0.01 mmol) and ethynylferrocene 3a (168 mg, 0.8 mmol) in dry degassed DCE (1 mL) was added a solution of the diyne 2a (36 mg, 0.2 mmol) in DCE (3 mL) over 15 min via a syringe at room temperature. The reaction mixture was stirred at ambient temperature for 1 h. After concentration in vacuo, the residue was purified by silica gel column flush chromatography (eluent, hexane:AcOEt = 48:1) to afford 4a (61 mg, 73%) as orange solids.
    • Typical experimental procedure. Synthesis of 4a: To a solution of Cp*RuC(cod) (3.8 mg, 0.01 mmol) and ethynylferrocene 3a (168 mg, 0.8 mmol) in dry degassed DCE (1 mL) was added a solution of the diyne 2a (36 mg, 0.2 mmol) in DCE (3 mL) over 15 min via a syringe at room temperature. The reaction mixture was stirred at ambient temperature for 1 h. After concentration in vacuo, the residue was purified by silica gel column flush chromatography (eluent, hexane:AcOEt = 48:1) to afford 4a (61 mg, 73%) as orange solids.
  • 18
    • 46249106894 scopus 로고    scopus 로고
    • All new compounds were fully characterized. 4a: mp. 159.2-159.9 °C; IR (CHCl3) 1735 cm-1; 1H NMR (300 MHz, CDCl3, 25 °C, δ 3.56 (s, 2 H, 3.62 (s, 2 H, 3.76 (s, 6 H, 4.04 (s, 5 H, 4.28 (t, J, 1. 8 Hz, 2 H, 4.58 (t, J, 1. 8 Hz, 2 H, 7. 10 (d, J, 7.5 Hz, 1 H, 7.28 (s, 1 H, 7.30 (d, J, 7.5 Hz, 1 H, 13C NMR (75 MHz, CDCl3, 25 °C, 8 40.45, 40.60, 53.02, 60.38, 66.51, 68.70, 69.54, 85.77, 121.78, 123.91, 125.16, 137.45, 137.96, 139.87, 171.99; MS (FAB, m/z, 418 (100, M, 358 (8, M+-H, CO2Me, 300 (12, M+-2CO2Me, EA calcd, ) for C22H22FeO4(418.26, C 65.05, H 5.30; found: C 65.98, H 5.19. 4b: mp. 178.3-178.9 °C; 1H NMR (300 MHz, CDCl3, 25 Γ, δ 2.40 (s, 3 H, 4.01 (s, 5 H, 4.30 (t, J, 2.0 Hz, 2 H, 4.57 (t, J, 2.0 Hz, 2 H, 4.58 s, 2 H, 4.62
    • 3, 25 °C): δ 4.20 (t, J = 2.0 Hz, 4 H), 4.20 (t, J = 1.8 Hz, 2 H), 4.22 (s, 10 H), 4.30 (s, 4 H)
  • 21
    • 0035803662 scopus 로고    scopus 로고
    • A monocyclic bis(ferrocenyl)ruthenacycle was reported, see: Yamada, Y.; Mizutani, J.; Kurihara, M.; Nishihara, H. J. Organomet. Chem. 2001, 637-639, 80.
    • A monocyclic bis(ferrocenyl)ruthenacycle was reported, see: Yamada, Y.; Mizutani, J.; Kurihara, M.; Nishihara, H. J. Organomet. Chem. 2001, 637-639, 80.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.