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2.6.4.5.2 Variation 2: Reaction of Organochromium(III) Compounds Prepared from Chromium(II) Chloride by Oxidative Addition (The Nozaki–Hiyama–Kishi Procedure)

DOI: 10.1055/sos-SD-002-00315

Poli, R.; Smith, K. M.Science of Synthesis, (20032311.

This methodology was pioneered by Hiyama[‌126‌] and refined by Kishi[‌127‌] and Nozaki.[‌128‌] The organochromium reagent is readily formed from chromium(II) salts upon one-electron oxidative addition (Section 2.6.4.2.1) of a wide range of substrates including al­lyl, propargyl, alkenyl, and aryl halides, alkenyl tri­fluo­ro­methane­sul­fo­nates, and al­lyl sul­fon­ates and phos­phates. The most convenient chromium(II) salt is the an­hy­dro­us chlo­ride, which can either be purchased or prepared in situ from chromium(III) chlo­ride and various reducing agents. The performance of the chromium(II) chlo­ride reagent in forming the CrC bond is enhanced by the addition of a catalytic amount of nickel(II) chlo­ride.[‌127‌,‌128‌]

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