Palladium-Catalyzed Triethylammonium Formate Reductions. 4. Reduction of Acetylenes to Cis Monoenes and Hydrogenolysis of Tertiary Allylic Amines

Article abstract of DOI:10.1021/jo01312a021

Eight phenyl-conjugated and double bond conjugated acetylenes were reduced with triethylammonium formate and a palladium on carbon catalyst.Cis olefins were obtained in good yields in five examples. 4-Nitrodiphenylacetylene gave only 4-aminodibenzyl and (Z)-methyl non-2-en-4-ynoate gave mainly the E,Z dienoate. 1-Phenyl-3-methylbut-3-en-1-yne gave the cis diene initially, but it isomerized partially under the reaction conditions.Five tertiary allylic amines were shown to undergo hydrogenolysis with the same reducing agent and catalyst to give mixtures of two isomeric olefins in moderate to good yields.