Electrochemical carboxylation of arylmethyl chlorides catalysed by [Co(salen)] [H2salen = N,N′-bis(salicylidene)ethane-1,2-diamine]

DOI: 10.1039/DT9960001613

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Journal of the Chemical Society, Dalton Transactions p. 1613 - 1618 (1996)

Update date:2022-07-30

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Authors:

Isse, Abdirisak Ahmed

Gennaro, Armando

Vianello, Elio

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Article abstract of DOI:10.1039/DT9960001613

The electrochemical carboxylation of some arylmethyl chlorides RCl [R = benzyl, 4-methoxybenzyl, 4-(trifluoromethyl)benzyl or diphenylmethyl] catalysed by [Co(salen)] [H₂salen = N,N′-bis(salicylidene)-ethane-1,2-diamine] was studied in acetonitrile. Comparable amounts of carboxylic acids and saturated hydrocarbons were obtained when R = PhCH₂ or 4-MeOC₆H₄CH₂ whereas carboxylic acids were the main products with R = 4-F₃CC₆H₄CH₂ or Ph₂CH. Electrogenerated [Co¹(salen)]^- reacts with RCl to give an organometallic complex, [Co^III(salen)R], with a rate constant which, for all chlorides investigated, is of the order of 10⁵ dm³ mol^-1 s^-1. The one-electron-reduced complex [Co^II(salen)R]^- is unstable and its decomposition in the presence of CO₂ is the key step of the electrocatalytic process. Different decomposition pathways are considered and their mechanistic implications discussed. In the presence of proton donors [Co^II(salen)R]^- undergoes rapid hydrolysis to RH and [Co(salen)].

Full text of DOI:10.1039/DT9960001613

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