메뉴 건너뛰기




Volumn 45, Issue 35, 2004, Pages 6615-6618

Highly selective synthesis of 1-(silyl)-1-(boryl)ethenes via a ruthenium-catalyzed silylative coupling reaction

Author keywords

Ruthenium complexes; Silylative coupling; Vinylboranes; Vinylsilanes

Indexed keywords

BORANE DERIVATIVE; ETHYLENE; RUTHENIUM;

EID: 4143069218     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.07.018     Document Type: Article
Times cited : (30)

References (30)
  • 1
    • 0034251446 scopus 로고    scopus 로고
    • I. Marek Chem. Rev. 100 2000 2887 2900
    • (2000) Chem. Rev. , vol.100 , pp. 2887-2900
    • Marek, I.1
  • 5
    • 0000390817 scopus 로고    scopus 로고
    • Organosilicon Compounds in Cross-Coupling Reactions
    • F. Diederich P. Stang Wileyâ€"VCH Weinheim
    • For recent reviews on the use of silyl olefins in cross-coupling reactions see: T. Hiyama Organosilicon Compounds in Cross-Coupling Reactions F. Diederich P. Stang Metal Catalyzed Cross-Coupling Reactions 1998 Wileyâ€"VCH Weinheim Chapter 10
    • (1998) Metal Catalyzed Cross-Coupling Reactions
    • Hiyama, T.1
  • 8
    • 2042507954 scopus 로고
    • For recent reviews on alkenylboranes in cross-coupling reactions see: N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457 2483
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura1    Suzuki, A.N.2
  • 16
    • 0037405684 scopus 로고    scopus 로고
    • For reviews on silylative coupling of vinylsilanes with olefins see: B. Marciniec, and C. Pietraszuk Curr. Org. Chem. 7 2003 691 743
    • (2003) Curr. Org. Chem. , vol.7 , pp. 691-743
    • Marciniec1    Pietraszuk, C.B.2
  • 22
    • 4143053889 scopus 로고    scopus 로고
    • note
    • 2 (0.02 mmol) and CuCl (0.10 mmol) were added. The reaction progress was monitored by GC. Analyses were made before adding the catalyst and every hour thereafter for the duration of the reaction. The extent of conversion of the substrates was calculated using the internal standard method
  • 23
    • 4143086247 scopus 로고    scopus 로고
    • note
    • 2 (0.22 mmol) and CuCl (1.1 mmol) were added (at ambient temp or at 0°C) and the reaction was carried out for 2 h. The catalyst was removed via column chromatography and products were isolated by vacuum distillation (yields are included in Table 1)
  • 24
    • 4143141177 scopus 로고    scopus 로고
    • note
    • +, 1%), 156 (14), 155 (100), 154 (32),127 (20), 126 (7), 111 (26), 110 (7), 101 (6), 73 (6), 59 (8), 45 (8)
  • 25
    • 4143118145 scopus 로고    scopus 로고
    • note
    • CuCl is suggested to act in the system as a phosphine scavenger
  • 27
    • 4143100558 scopus 로고    scopus 로고
    • note
    • 2 (200 mg, 0.24 mmol) in benzene (5 mL) and the reaction mixture was refluxed for 24 h. The solvent was evaporated under reduced pressure and 2 mL of cold hexane (-50°C) was added. The supernatant was removed and the yellow precipitate was washed twice with hexane (at -50°C) and dried in vacuo. Yield 15% (not optimized)
  • 28
    • 4143086248 scopus 로고    scopus 로고
    • note
    • 1H NMR at room temp


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.