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Volumn , Issue 11, 2008, Pages 1690-1692

Transition-metal-free conjugate stannyl transfer to α,β- unsaturated carbonyl and carboxyl compounds in basic aqueous media

Author keywords

Aqueous media; Conjugate addition; Interelement linkages; Silicon; Tin

Indexed keywords

CARBONYL DERIVATIVE; CARBOXYL GROUP; SILICON DERIVATIVE; TRANSITION ELEMENT;

EID: 48249149956     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078493     Document Type: Article
Times cited : (6)

References (36)
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    • General Procedure for Conjugate Stannylation: Under an inert atmosphere, a flame-dried Schlenk tube was charged with the indicated α,β-unsaturated acceptor A (0.10 mmol, 1.0 equiv) and the THF-H 2O solvent mixture (20:1, 2.1 mL, The base MX (0.1 mmol, 1.0 equiv) as well as B (1, 0.25 mmol, 2.5 equiv) were added, and the reaction mixture was heated to 50 °C. Conversion was monitored by TLC. After full consumption of A the reaction mixture was diluted with tert-butylmethylether (10 mL) at r.t. A small portion of silica gel was added and the solvents were removed in vacuo. The crude product C on silica gel was then subjected to flash chromatography on Et3N-deactivated silica gel using cyclohexane-tert-butylmethylether solvent mixtures. Stannanes C 22-95, were isolated as colorless oils
    • 3N-deactivated silica gel using cyclohexane-tert-butylmethylether solvent mixtures. Stannanes C (22-95%) were isolated as colorless oils.
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    • Reagent 1 is not particularly volatile, stable towards GLC measurements, and provides easy-to-interpret NMR spectra.
    • Reagent 1 is not particularly volatile, stable towards GLC measurements, and provides easy-to-interpret NMR spectra.
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    • Preparation of Dimethylphenyl(trimethylsilyl)stannane (1, Neat dimethylphenylstannyl chloride19 (3.00 g, 11.5 mmol, 1.00 equiv) was added dropwise to Me3SiCl-activated lithium (large excess) in THF (40 mL) at 0 °C under ultrasonic irradiation, and the reaction mixture was then maintained at these conditions for 2 h. The supernatant blue-black-colored solution was subsequently transferred to another flask and slowly treated with trimethylsilyl chloride (3.10 mL, 24.3 mmol, 2.10 equiv) at 0 °C. After stirring at ambient temperature for additional 3 h, the solvent was removed under reduced pressure. Crude 1 was purified by flash chromatography on silica gel using cyclohexane as solvent. The title compound (3.22 g, 10.8 mmol, 94, was obtained as a colorless oil. IR (ATR, 3062 (w, 2950 (w, 2893 (w, 1427 (m) cm-1. 1H NMR 300 MHz, CDCl3, δ, 0.26 [t, 2JH,Sn, 2
    • 20SiSn: C, 44.18; H, 6.74. Found: C, 44.30; H, 7.01.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.