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Nozaki-Hiyama-Kishi (NHK) coupling

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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.

 

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Points for discussion:

Why the substrates were dried before the reaction?

Written by pmgb

April 24, 2008 at 1:07 am