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Volumn 36, Issue 1, 2007, Pages 14-15

A convenient, catalyst-free cross-coupling reaction of α-sulfur- substituted alkylstannanes with acid chlorides leading to α-sulfur- substituted ketones

(2) Kagoshima, Hirotaka a Takahashi, Naoshi a

a IBARAKI UNIVERSITY (Japan)

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EID: 34247267205 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2007.14 Document Type: Article

Times cited : (6)

References (22)

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- These stannanes were prepared by nucleophilic substitution of sulfur nucleophiles with methanesulfonates of α-hydroxy alkylstannanes. A representative procedure for 2a: To a cooled (0°C) solution of tributyl(l-hydroxybutyl)stannane (5.7 g, 16mmol, which was prepared from butanal and tributyl-stannyllithium by the literature procedure,5b in CH2Cl2 (40 mL) was added Et3N (2.8 mL, 20 mmol) and methanesulfonyl chloride (1.3 mL, 17 mmol, sequentially. The reaction mixture was stirred for 2 h at this temperature and then the reaction was quenched with an ice-water mixture. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were washed with saturated aqueous NaHSO4 solution followed by brine, dried over Na2SO4. Concentration under reduced pressure afforded the corresponding methanesulfonate 6.9 g, 97, To a mixture
- 4, and concentrated. Column chromatography (hexane) followed by Kugelrohr distillation (190°C/0.3mmHg) afforded 2a (4.9g, 78%).

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22
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- A typical experimental procedure (Table 3, Entry 1): A mixture of la (17mg, 0.12mmol) and 2a (48mg, 0.10 mmol) in mesitylene (1.5 mL) was refluxed for 1 h. The resulting mixture was diluted with hexane (1 mL) and passed through a silica gel short column to remove the bulk of mesitylene (hexane to hexane/AcOEt = 5/1). The crude product was purified by preparative thin layer chromatography (hexane/AcOEt = 5/l) to give 3a(26mg, 87%).
- A typical experimental procedure (Table 3, Entry 1): A mixture of la (17mg, 0.12mmol) and 2a (48mg, 0.10 mmol) in mesitylene (1.5 mL) was refluxed for 1 h. The resulting mixture was diluted with hexane (1 mL) and passed through a silica gel short column to remove the bulk of mesitylene (hexane to hexane/AcOEt = 5/1). The crude product was purified by preparative thin layer chromatography (hexane/AcOEt = 5/l) to give 3a(26mg, 87%).

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