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Please login or sign up for a free trial to access the full content. Variation 4: Using Stoichiometric Amounts of Carbonylferrate Salts and an Acidic Workup

DOI: 10.1055/sos-SD-025-00209

Hashmi, A. S. K.Science of Synthesis, (200725329.

Commercially available disodium tetracarbonylferrate (44),[‌120‌] for which an excellent preparative procedure is available,[‌121‌] can be used instead of a carbonylhydridoferrate, but the acyl complex that is formed after alkylation is anionic, and acid treatment is required to liberate the aldehyde 45 (Scheme 12).[‌122‌] Triphenylphosphine can also be added to facilitate the workup.[‌121‌] Ester groups on the substrate are tolerated.[‌122‌] Electrochemical reduction of pentacarbonyliron(0) in acetonitrile, followed by the subsequent addition of an alkyl halide and an acid, also gives the corresponding aldehyde.[‌123‌] Detailed studies have been made of both the oxidative addition[‌124‌] and the alkyl migration[‌125‌,‌126‌] steps in the reaction of the ferrates with alkyl halides.

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Me(MM8)8MM(Me)Me MeMM/Me8M 88 [‌888‌]
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