The anodic oxidation of boronic acids—I. n-butaneboronic acid: product yields and comparison with pentanoic acid

Humffray, A.A.; Williams, L.F.G.

doi:10.1016/0013-4686(72)80039-2

Cited by 10 publications

(3 citation statements)

References 25 publications

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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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Section: Introductionmentioning

confidence: 99%

Electrochemical Oxidation of Organotrifluoroborate Compounds

2016

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“…However, to our knowledge, there have been only limited examples of electrochemical oxidation of organoboron compounds to date . Anodic oxidation of alkylboronic acids in aqueous NaOH solution resulted in formation of the corresponding dimers or olefins via radical or cation intermediates . Later, Suzuki and his co‐workers also reported that anodic oxidation of trialkylboranes in NaOMe/MeOH and NaOAc/AcOH generated alkyl radical or cation species, which resulted in radical coupling or nucleophilic substitutions with methoxide and acetate ions depending on anode materials .…”

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.

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“…Anodic oxidation of alkylboronic acids was also carried out in an aqueous NaOH solution to afford the corresponding dimers or olefins via radical or cation intermediates. [27][28][29] Becker and his coworkers reported anodic oxidation of arylboronic acid esters in the presence of bromide ions leading to the cleavage of the carbon-boron bond to provide the corresponding aryl bromides in moderate yields. 30 In this reaction, the generation of bromonium ion was proposed for the bond cleavage.…”

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confidence: 99%

Electrochemical Properties and Reactions of Organoboronic Acid Esters Containing Unsaturated Bonds at Their α-Position

Ohtsuka

Inagi

2016

J. Electrochem. Soc.

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Electrochemical analyses of 2-(cynnamyl)boronic acid pinacol ester and (3-phenyl-2-propynyl)boronic acid pinacol ester, and their trimethylsilyl analogues as well as their parent compounds were comparatively studied by cyclic voltammetry measurements. We found remarkable negative shifts of the oxidation potentials of the organoboronic acid pinacol esters in the presence of fluoride ions compared to those in the absence of fluoride ions. The negative shift observed was more pronounced than that of the corresponding trimethylsilyl compounds. Such marked negative shift seems to be derived from the formation of negatively charged boron-ate complex with fluoride ions as well as β-effect of organoborate. Anodic acetoxylation of organoboronic acid pinacol esters was achieved in NaOAc/AcOH, while their alkoxylation was successfully carried out in the presence of fluoride ions.

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The anodic oxidation of boronic acids—I. n-butaneboronic acid: product yields and comparison with pentanoic acid

Cited by 10 publications

References 25 publications

Electrochemical Oxidation of Organotrifluoroborate Compounds

Electrochemical Oxidation of Organotrifluoroborate Compounds

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

Electrochemical Properties and Reactions of Organoboronic Acid Esters Containing Unsaturated Bonds at Their α-Position

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