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Volumn , Issue 6, 2008, Pages 845-848

Sequential electrophilic trapping reactions for the desymmetrization of dilithio(hetero)arenes

Author keywords

Arenes; Bromine lithium exchange; Dianions; Heterocycles; One pot reactions

Indexed keywords

BROMINE; LITHIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

EID: 42149124365     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1042911     Document Type: Article
Times cited : (8)

References (30)
  • 1
    • 33845552740 scopus 로고
    • For selected reviews on halogen-metal exchange, see for example: a
    • For selected reviews on halogen-metal exchange, see for example: (a) Parham, W. E.; Bradsher, C. K. Acc. Chem. Res. 1982, 15, 300.
    • (1982) Acc. Chem. Res , vol.15 , pp. 300
    • Parham, W.E.1    Bradsher, C.K.2
  • 10
    • 84890597202 scopus 로고    scopus 로고
    • For a recent monography, see for example:, Zhu, J, Bienaymé, H, Eds, Wiley-VCH: Weinheim
    • For a recent monography, see for example: Multicomponent Reactions; Zhu, J.; Bienaymé, H., Eds.; Wiley-VCH: Weinheim, 2005.
    • (2005) Multicomponent Reactions
  • 18
    • 3042799070 scopus 로고    scopus 로고
    • For reviews on diversity-oriented syntheses, see for example: a
    • For reviews on diversity-oriented syntheses, see for example: (a) Schreiber, S. L.; Burke, M. D. Angew. Chem. Int. Ed. 2004, 43, 46.
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 46
    • Schreiber, S.L.1    Burke, M.D.2
  • 25
    • 42149179732 scopus 로고    scopus 로고
    • Representative Procedure, Synthesis of Trimethyl[5-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl]silane (3b; Table 1, Entry 2) In a flame-dried Schlenk flask under N2 atmosphere n-BuLi (2.5 M in n-hexane, 0.83 mL, 2.00 mmol) and TMEDA (0.3 mL, 2.0 mmol) were dissolved in anhyd THF (30 mL) at -78°C. 2,5-Dibromothiophene (1a, 242 mg, 1.00 mmol) was added slowly to the solution, and the mixture was stirred for 30 min. Then, TMSCl (2a, 0.11 g, 1.00 mmol) in anhyd THF (10 mL) was added dropwise to the stirred solution over a period of 3 h. The reaction mixture was stirred for another 30 min and B(OMe)3 (2c, 208 mg, 1.00 mmol) was added. After stirring for 40 min pinacol (130 mg, 1.10 mmol) in anhyd THF (5 mL) was added to the mixture. The solution was allowed to warm to r.t, a few drops of AcOH were added, and the solution was stirred for 14 h. After aqueous workup and extraction with Et2O the com
    • 3)
  • 26
    • 42149092052 scopus 로고    scopus 로고
    • Interestingly, the expected byproducts, i.e. symmetrical disubstitution with the first electrophile and monosubstitution with the first electrophile followed by proton quenching are only found in minor quantities and were identified by GC-MS analysis in the crude ethereal extract during workup
    • Interestingly, the expected byproducts, i.e. symmetrical disubstitution with the first electrophile and monosubstitution with the first electrophile followed by proton quenching are only found in minor quantities and were identified by GC-MS analysis in the crude ethereal extract during workup.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.