Metal-Free tert-Butyl Hydrogenperoxide (TBHP) Mediated Radical Alkylation of Enol Acetates with Alcohols: A New Route to β-Hydroxy Ketones

Abstract

A metal-free TBHP-mediated radical alkylation of enol acetates with alcohols is described. This method provides a new route to a variety of β-hydroxy-ketones in moderate to good yields.

Dehalogenative Deuteration of Unactivated Alkyl Halides Using D2O as the Deuterium Source

“…1 H NMR (400 MHz, CDCl 3 ): δ 7.97–7.94 (m, 2H), 7.60–7.55 (m, 1H), 7.48–7.44 (m, 2H), 4.16–4.12 (m, 1H), 3.37 (d, J = 3.2 Hz, 1H), 3.17 (dd, J = 17.6 Hz, 2.8 Hz, 1H), 3.04 (dd, J = 17.6, 8.8 Hz, 1H), 1.67–1.55 (m, 2H), 1.01 (t, J = 7.2 Hz, 3H); 13 C­{ 1 H} NMR (100 MHz, CDCl 3 ): δ 200.9, 136.7, 133.4, 128.6, 128.0, 69.0, 44.5, 29.3, 9.9. The spectroscopic data are in agreement with that previously reported …”

“…The spectroscopic data are in agreement with that previously reported. 31 To a solution of s-1i (1.78 g, 10 mmol) in CHCl 3 (30 mL) was added dropwise PBr 3 (0.47 mL, 5 mmol) at 0 °C under air. The mixture was warmed to room temperature and stirred for 20 h. After the starting material was completely consumed, the mixture was quenched with water, extracted with ethyl acetate, washed with saturated NaHCO 3 solution, and dried over anhydrous Na 2 SO 4 .…”