Archive for the ‘Nozaki-Hiyama-Kishi coupling’ Category
Nozaki-Hiyama-Kishi (NHK) coupling
To a mixture of aldehyde (0.0404 mmol) and vinyl iodide (0.162 mmol) (dried azeotropically using benzene, 2 × 2 mL) in anhydrous DMSO (1.3 mL) was added to 1% (w/w) NiCl2 in CrCl2 (49.6 mg) under N2. The resulting mixture was stirred in dark for 13 h at rt, then diluted with aq. saturated NH4Cl (5 mL). The aq. phase was extracted with DCM (6 × 5 mL) and the combined organic layers were then washed with aq. sat. NH4Cl (5 mL), dried (Na2SO4), filtered, concentrated and the residue was purified by column chromatography to give the 2 diastereomers in a total of 70% yield.
Source: Toste, Radosevich, Chan and Shih, ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200800554.
Points for discussion:
Why the substrates were dried before the reaction?