The Reaction of Organolithium Compounds with Nickel Carbonyl

Carboxylation and Esterification of Functionalized Arylcopper Reagents

“…8,9 The nickel catalyst is capable of producing aryl acids but suffers from the drawback of the acute toxicity of Ni(CO) 4 . 10 By comparison, arylcopper compounds readily undergo carboxylation with CO 2 and the toxicity of copper salts is much less than that of nickel compounds.…”

“…Several workers have developed reactions of transition-metal carbonyl catalysts capable of producing acids and esters from suitable feedstocks. The Na 2 Fe(CO) 4 system was studied by Cooke and Collman, NaCo(CO) 4 by Heck et al, and Ni(CO) 4 by Tsutsumi and co-workers to name a few. In most cases aliphatic acids and esters could be produced in high yields, but vinyl and aryl systems were unreactive. , The nickel catalyst is capable of producing aryl acids but suffers from the drawback of the acute toxicity of Ni(CO) 4 .…”

“…The Na 2 Fe(CO) 4 system was studied by Cooke and Collman, NaCo(CO) 4 by Heck et al, and Ni(CO) 4 by Tsutsumi and co-workers to name a few. In most cases aliphatic acids and esters could be produced in high yields, but vinyl and aryl systems were unreactive. , The nickel catalyst is capable of producing aryl acids but suffers from the drawback of the acute toxicity of Ni(CO) 4 . By comparison, arylcopper compounds readily undergo carboxylation with CO 2 and the toxicity of copper salts is much less than that of nickel compounds.…”

Reactivity of a Nickel Acylate Complex with Acetylenes under an Ar and a CO Atmosphere

“…In contrast to the large number of papers that deal with the reactions of Fischer-type carbene complexes and related systems with acetylenes, the number of publications dealing with the reactions of acylate complexes with acetylenes is limited. Approximately thirty years ago, the reaction of a variety of nickel acylate complexes with monosubstituted acetylenes in Et 2 O (Scheme ) was first reported. , When the reaction was kept at −70 °C, the sole product was a 1,4-diketone ( 9 ), the same type of product we have obtained from the reactions of 1 with vinyl halides ( 7 ) 2b…”