Anodic carbon–boron bond cleavage through the intermediacy of electrogenerated bromonium ion

Shi, Dashuang; Gitkis, Anna; Becker, James Y.

doi:10.1016/j.electacta.2007.08.028

Cited by 13 publications

(8 citation statements)

References 33 publications

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“…The synthetically useful species chloronium (Cl + ), 88 chlorine atom (Cl ∑ ), 89 bromonium (Br + ), 90 or iodonium (I + ), 91 can be electrogenerated at the anode in an electrochemical cell using the corresponding anions as starting materials. These free radical or positively charged intermediates can participate in halogenation, oxidation or cleavage reactions regenerating the starting anions, which are then reoxidized in an electrocatalytic cycle (Fig.…”

Section: The Use Of Halogenonium Ions (X + ) As Oxidants In Synthesismentioning

confidence: 99%

Organic electrosynthesis: a promising green methodology in organic chemistry

et al. 2010

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Section: The Use Of Halogenonium Ions (X + ) As Oxidants In Synthesismentioning

confidence: 99%

Organic electrosynthesis: a promising green methodology in organic chemistry

et al. 2010

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“…Organoboron compounds are highly useful for modern synthetic organic chemistry and pharmaceutical chemistry as well as materials science . In addition, the electrochemistry of triorganoboranes has been studied mainly from a synthetic aspect to date …”

Section: Introductionmentioning

confidence: 99%

Electrochemical Oxidation of Organotrifluoroborate Compounds

2016

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Electrochemical analyses of various organotrifluoroborates, and the corresponding boronic acids and esters, were comparatively studied by using cyclic voltammetry. The organotrifluoroborates were found to have much lower oxidation potentials compared with the latter two types of compounds. We also found a pronounced β‐effect for allyltrifluoroborate, which was indicated by both experimental and theoretical aspects. Such a β‐effect is similar to that of allyltrimethylsilane. Anodic oxidation of n‐decyltrifluoroborate at a platinum anode gave a radical coupling product in moderate yield, eliminating a boryl moiety. Anodic acetoxylation of phenethyl‐, aryl‐, and styryltrifluoroborates was also successfully carried out at a graphite anode in NaOAc/AcOH to provide the acetoxylated products in good to moderate yields although a large excess of electricity was required.

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“…Such anode dependency in product selectivity is quite similar to the Kolbe electrolysis. Becker and his coworkers reported that anodic oxidation of arylboronate esters in the presence of bromide ions resulted in the cleavage of the carbon‐boron bond to provide the corresponding aryl bromides in moderate yields . The anodic generation of bromonium ions has been proposed for the initial step of the reaction.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Properties and Reactions of Organoboronic Acids in the Presence of Fluoride Ions

et al. 2016

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Electrochemical analyses of alkyl, phenyl, and thienylboronic acids were comparatively studied by cyclic voltammetric measurements in the absence and presence of fluoride ions, and we found remarkable negative shift of their oxidation potentials in the presence of fluoride ions compared with those in the absence of fluoride ions. Such negative shift seems to be derived from the formation of negative charged boron‐ate complex with fluoride ions. Anodic fluorination of 2‐acetyl‐5‐thienylboronic acid was carried out to provide mono‐ and trifluoro products eliminating a boryl group in moderate yields. These results clearly indicate that a boryl group with fluoride ions is a good electroauxiliary.

show abstract

Anodic carbon–boron bond cleavage through the intermediacy of electrogenerated bromonium ion

Cited by 13 publications

References 33 publications

Organic electrosynthesis: a promising green methodology in organic chemistry

Organic electrosynthesis: a promising green methodology in organic chemistry

Electrochemical Oxidation of Organotrifluoroborate Compounds

Electrochemical Properties and Reactions of Organoboronic Acids in the Presence of Fluoride Ions

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