Synthesis of tetrahydrofluorenes from the cycloadduct of 3-ethynyl-5-bromo-2-pyrone via cyclocarbopalladation reactions

Tetrahedron Letters

Volumn 44, Issue 24, 2003, Pages 4439-4442

  Min, Soo Hyun ^a   Pang, Soo Jin ^a   Cho, Cheon Gyu ^a  

^a Hanyang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

3 ETHYNYL 5 BROMO 2 PYRONE; ALKENE DERIVATIVE; BORON; FLUORENE DERIVATIVE; ORGANOTIN COMPOUND; PYRONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; CYCLOADDITION; CYCLOCARBOPALLADATION; DIELS ALDER REACTION; DRUG SYNTHESIS; GEOMETRY; STEREOCHEMISTRY; THERMOSTABILITY;

EID: 0038066159     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01032-3     Document Type: Article

References (18)

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15. 4 (10 mol%) and 130 mg (0.35 mmol) of tributylvinyltin dissolved in 1.0 mL of anhydrous toluene at rt. After 1 h at 100°C, the reaction mixture was concentrated and chromatographed (hexanes:EtOAc, 5:1) to furnish 29 mg of the product 8d in 90% yield.
16. 3 (1 M) under Ar atmosphere at rt. After 1 h at 100°C, the reaction mixture was concentrated and chromatographed (hexanes:EtOAc, 5:1) to furnish 37 mg of the product 8e in 82% yield.
17. 4, filtered, concentrated and chromatographed (hexanes:EtOAc, 5:1) to provide 28 mg of 9e in 70% yield.
18. 13C NMR, FT-IR and HRMS.