An efficient protocol for the generation of carbon monoxide by Zn-mediated reduction of oxalyl chloride has been developed. Oxalyl chloride was applied as an extremely effective substitute for toxic gaseous CO in the palladium-catalyzed alkoxy-/amino-/hydrogen-/hydroxycarbonylation processes providing industrially interesting esters, amides, aldehydes, and carboxylic acids in good to excellent yields. This new procedure can be applied to various carbonylation reactions in the presence of a transition metal catalyst under mild conditions and with a stoichiometric amount of CO source.
We report substantially improved reaction conditions for palladium(II)-catalyzed tandem cyclization-intramolecular oxycarbonylation of (amino)polyols with a terminal double bond, based on utilization of iron pentacarbonyl [Fe(CO) 5 ] as an affordable and safe liquid supply of the carbonyl unit fully replacing gaseous carbon monoxide. Direct comparison with the classical version on a series of previously published substrates illustrates invariably shorter reaction times but comparable yields and selectivity.
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