Sustainable and Scalable Electrochemical Decarboxylative Cyanation of an Amino Acid Using KCN as Both Cyanide Source and Base
- 1School of Chemistry and Molecular Biosciences
- 2University of Queensland
Abstract
Organic nitriles are an important class of compounds found in pharmaceuticals and agrochemicals, as well as useful intermediates in synthesis. Decarboxylative cyanation as a method to generate nitriles enables the use of widely available carboxylic acids as starting materials. Although this method has been well-explored synthetically, current methodologies often feature poor atom economy or require harsh reaction conditions. Herein, an electrochemical method for the decarboxylative cyanation of Cbz-protected alanine that uses inexpensive KCN as the cyanide source has been developed. The operationally simple procedure only requires electrolyzing a mixture of the amino acid with the cyanide in DMSO/EtOH as the solvent, without any additional chemicals such as base or supporting electrolyte, resulting in excellent green chemistry metrics. Using inexpensive graphite and stainless-steel as electrodes, excellent conversion and selectivity towards the desired nitrile product were obtained. Translation of the process to a flow electrolysis cell confirmed that the electrochemical protocol is scalable. Thus, gram amounts of material were obtained in a parallel plate reactor, with a space-time yield of 1026 g L-1 h-1. The space-time yield in the flow system was ca. 70 times larger than its batch counterpart, confirming the suitability of flow electrolysis cells for scale-up purposes.
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BibTeX
@misc{giang2026sustainable,
title = {{Sustainable and Scalable Electrochemical Decarboxylative Cyanation of an Amino Acid Using KCN as Both Cyanide Source and Base}},
author = {Peter D. Giang and Cristóbal Hormazábal-Campos and David Cantillo},
howpublished = {ChemRxiv},
year = {2026},
month = oct,
doi = {10.26434/chemrxiv.15011156/v1},
url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15011156/v1},
note = {CC BY},
}
RIS
TY - UNPB
TI - Sustainable and Scalable Electrochemical Decarboxylative Cyanation of an Amino Acid Using KCN as Both Cyanide Source and Base
AU - Peter D. Giang
AU - Cristóbal Hormazábal-Campos
AU - David Cantillo
PY - 2026
DA - 2026/10/27
PB - ChemRxiv
DO - 10.26434/chemrxiv.15011156/v1
UR - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15011156/v1
AB - Organic nitriles are an important class of compounds found in pharmaceuticals and agrochemicals, as well as useful intermediates in synthesis. Decarboxylative cyanation as a method to generate nitriles enables the use of widely available carboxylic acids as starting materials. Although this method has been well-explored synthetically, current methodologies often feature poor atom economy or require harsh reaction conditions. Herein, an electrochemical method for the decarboxylative cyanation of Cbz-protected alanine that uses inexpensive KCN as the cyanide source has been developed. The operationally simple procedure only requires electrolyzing a mixture of the amino acid with the cyanide in DMSO/EtOH as the solvent, without any additional chemicals such as base or supporting electrolyte, resulting in excellent green chemistry metrics. Using inexpensive graphite and stainless-steel as electrodes, excellent conversion and selectivity towards the desired nitrile product were obtained. Translation of the process to a flow electrolysis cell confirmed that the electrochemical protocol is scalable. Thus, gram amounts of material were obtained in a parallel plate reactor, with a space-time yield of 1026 g L-1 h-1. The space-time yield in the flow system was ca. 70 times larger than its batch counterpart, confirming the suitability of flow electrolysis cells for scale-up purposes.
ER -