Abstract
An efficient route to silyl esters by dehydrogenative cross-coupling of silanes and
carboxylic acids was investigated. Treatment of silanes and carboxylic acids in the
presence of 15mol% of ZnCl2 in DMF at 120 °C afforded the corresponding silyl esters in good yields under relatively
mild conditions.
Key words
silyl esters - zinc chloride - silanes - carboxylic acids
References and Notes
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Typical Procedure.
2 (3 mmol, 0.40 g, 0.15 equiv, dried over P2 O5 under reduced pressure at r.t. for 24 h) under a nitrogen atmosphere at r.t. The
reaction mixture was stirred at 120 °C for 24 h (monitored by GC). The desired triethylsilyl
acetate was obtained as a colorless oil (yielding: 80%) after distillation under reduced
pressure (run 1).5c -1 . 1 H NMR (400 MHz, CDCl3 ): δ = 0.72 (6 H, q, J = 8.0 Hz), 0.93 (9 H, t, J = 8.0 Hz), 2.05 (3 H, s). 13 C NMR (100 MHz, CDCl3 ): δ = 4.21, 6.30, 22.35, 171.20.
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All of the silyl esters are known compounds and were compared with authentic samples
(prepared by cross-coupling of carboxylic acids and chlorosilanes in the presence
of Et3 N in CH2 Cl2 ). Identification was based on their IR, 1 H NMR and GCMS spectral data.
