Abstract
Cobalt-Salen mediated electroreductive and regioselective alkylation of electron deficient olefins is reported in one step in an undivided electrochemical cell, in the presence of an iron rod as sacrificial anode. Although the reactivity depends on the class of alkyl halides, the reported study offers a green and expeditious electrosynthetic route for Csp3-Csp3 bond formation in mild conditions. This study also confirms the possible formation of the heterobinuclear cobalt-Salen-iron complex previously reported as the effective catalyst.
Highlights
In the context of sustainable organic chemistry, electrosynthesis has gained a renewable interest because of its relevant green aspects [1,2,3]. is versatile process involves electrons as clean surrogates of dangerous, toxic, hazardous reductive or oxidative reagents
Various papers of our laboratory report the activation of aryl halides under cobalt or nickel catalysis for Csp2-Csp2 bond formation [4,5,6] or Csp2-Csp3 bond formation [7, 8] by using the sacrificial anode process [9]
Us, in the course of our work on the electrochemical activation of organic halides using the sacrificial anode process [9], we have found that alkylation of activated olefins can be carried out with a simple and cheap cobalt complex formed in situ. is allowed us to show that the combined use of cobalt-Salen with the undivided electrochemical cell process offers substantial advantages in the reductive coupling of 2-bromooctane and methyl vinyl ketone (MVK) [27]
Summary
In the context of sustainable organic chemistry, electrosynthesis has gained a renewable interest because of its relevant green aspects [1,2,3]. is versatile process involves electrons as clean surrogates of dangerous, toxic, hazardous reductive or oxidative reagents. Is can be circumvented advantageously by activation of the alkyl halide by a transition metal complex and its further reaction with the electrophile Such reactions can be carried out in one step procedure, in mild conditions. Us, in the course of our work on the electrochemical activation of organic halides using the sacrificial anode process [9], we have found that alkylation of activated olefins can be carried out with a simple and cheap cobalt complex formed in situ. We report here a systematic study of some examples of reductive coupling of alkyl halides and activated olefins using cobalt complexes to assess the influence of the experimental parameters (ligand, solvent, temperature, and electrolysis conditions) in order to optimize the yield and to get a better insight into the electroassisted catalytic mechanism
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