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25.1.4.1.5 Method 5: Reduction Using Tributyltin Hydride

DOI: 10.1055/sos-SD-025-00031

Harcken, C.Science of Synthesis, (20072570.

Trialkyltin hydrides and triaryltin hydrides react with acid chlorides without transition-metal catalysis to give aldehydes at room temperature or higher temperature in moderate yields.[‌42‌] The only application this reaction has found is in the preparation of α-oxoaldehydes[‌43‌,‌44‌] and glyoxalic acid esters.[‌45‌] The palladium-catalyzed variation of this reaction has been reported and has found some applications, e.g. the synthesis of aldehyde 16 from acid chloride 15 (see Scheme 8).[‌46‌] The conditions are milder and the yields are generally higher.[‌47‌] Esters and carbamates are not reduced under the conditions.[‌47‌‌49‌] α,β-Unsaturated acid chlorides can be overreduced to the saturated aldehydes.[‌50‌]

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