Regioselectivity of Electrochemical C-H Functionalization Via Iminium Ion

The electrochemical Shono oxidation of Boc‐protected cyclic amines was revised. The conditions for scalable electrochemical synthesis of cyclic enecarbamates were found. The developed protocol included recycling of the full range of used reagents, favoring to E‐factor reduction according to Green Chemistry requirements. The method opened the way for the convenient preparation of previously uncommon materials, which could become useful synthetic intermediates. Their synthetic potential was evaluated in [2+1] and [2+2] cycloadditions as well as electrophilic functionalization. Moreover, functionalized enecarbamates with carbonyl groups in β‐position were used as latent 1,3‐bielectrophiles in classical heterocyclizations. In a case of the hydrazine, the corresponding unusually decorated pyrazoles were prepared. The proposed methodology is a straightforward tool for the design and synthesis of Medicinal Chemistry relevant building blocks. As examples, 5‐fluoro pipecolic and 3‐fluoro isonipecotic acids were synthesized starting from Boc‐protected esters of the pipecolic and the isonipecotic acids respectively; the 5‐step approach to pyrazole containing α‐aminoacids with different linkers between the aminoacidic and pyrazole moieties was elaborated based on the cheapest commercially available racemic and chiral cyclic α‐aminoacids; the convenient approach to the functionalized tetrahydropyrido[3,4‐d]pyridazines was proposed starting from Boc‐protected ester of the isonipecotic acids.magnified image

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Electrochemical Scaled‐up Synthesis of Cyclic Enecarbamates as Starting Materials for Medicinal Chemistry Relevant Building Bocks

Tereshchenko

Perebiynis

Knysh

et al. 2020

Adv Synth Catal

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The Effect of Ring-Size on the Anodic Oxidation of ‘Cyclic Amides’ in Methanol

Golub

Becker

2016

Electrochimica Acta

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Study of Electrochemical Oxidation and Quantification of the Pesticide Pirimicarb Using a Boron-Doped Diamond Electrode

Selva

Araújo

Bacil

et al. 2017

Electrochimica Acta

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Regioselectivity of Electrochemical C-H Functionalization Via Iminium Ion

Cited by 3 publications

References 37 publications

Electrochemical Scaled‐up Synthesis of Cyclic Enecarbamates as Starting Materials for Medicinal Chemistry Relevant Building Bocks

Electrochemical Scaled‐up Synthesis of Cyclic Enecarbamates as Starting Materials for Medicinal Chemistry Relevant Building Bocks

The Effect of Ring-Size on the Anodic Oxidation of ‘Cyclic Amides’ in Methanol

Study of Electrochemical Oxidation and Quantification of the Pesticide Pirimicarb Using a Boron-Doped Diamond Electrode

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