Paired Electrolysis for Decarboxylative Cyanation: 4-CN-Pyridine, a Versatile Nitrile Source

Gadde Sathish Kumar; Prashant S. Shinde; Haifeng Chen; Krishnamoorthy Muralirajan; Rajesh Kancherla; Magnus Rueping

doi:10.1021/acs.orglett.2c01897

Paired Electrolysis for Decarboxylative Cyanation: 4-CN-Pyridine, a Versatile Nitrile Source

Gadde Sathish Kumar, Prashant S. Shinde, Haifeng Chen, Krishnamoorthy Muralirajan, Rajesh Kancherla, Magnus Rueping^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

A decarboxylative cyanation of amino acids under paired electrochemical reaction conditions has been developed. 4-CN-pyridine was found to be a new and effective cyanation reagent under catalyst-free conditions. Mechanistic studies support a nucleophilic reaction pathway, and the cyanation protocol can be applied to diverse substrates including N,N-dialkyl aniline and indole derivatives.

Original language	English (US)
Pages (from-to)	6357-6363
Number of pages	7
Journal	Organic Letters
Volume	24
Issue number	35
DOIs	https://doi.org/10.1021/acs.orglett.2c01897
State	Published - Sep 9 2022

Bibliographical note

Funding Information:
This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/4384).

Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Paired Electrolysis for Decarboxylative Cyanation: 4-CN-Pyridine, a Versatile Nitrile Source",

abstract = "A decarboxylative cyanation of amino acids under paired electrochemical reaction conditions has been developed. 4-CN-pyridine was found to be a new and effective cyanation reagent under catalyst-free conditions. Mechanistic studies support a nucleophilic reaction pathway, and the cyanation protocol can be applied to diverse substrates including N,N-dialkyl aniline and indole derivatives.",

author = "Kumar, {Gadde Sathish} and Shinde, {Prashant S.} and Haifeng Chen and Krishnamoorthy Muralirajan and Rajesh Kancherla and Magnus Rueping",

note = "Funding Information: This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/4384). Publisher Copyright: {\textcopyright} 2022 American Chemical Society. All rights reserved.",

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doi = "10.1021/acs.orglett.2c01897",

language = "English (US)",

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T1 - Paired Electrolysis for Decarboxylative Cyanation

T2 - 4-CN-Pyridine, a Versatile Nitrile Source

AU - Kumar, Gadde Sathish

AU - Shinde, Prashant S.

AU - Chen, Haifeng

AU - Muralirajan, Krishnamoorthy

AU - Kancherla, Rajesh

AU - Rueping, Magnus

N1 - Funding Information: This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/4384). Publisher Copyright: © 2022 American Chemical Society. All rights reserved.

PY - 2022/9/9

Y1 - 2022/9/9

N2 - A decarboxylative cyanation of amino acids under paired electrochemical reaction conditions has been developed. 4-CN-pyridine was found to be a new and effective cyanation reagent under catalyst-free conditions. Mechanistic studies support a nucleophilic reaction pathway, and the cyanation protocol can be applied to diverse substrates including N,N-dialkyl aniline and indole derivatives.

AB - A decarboxylative cyanation of amino acids under paired electrochemical reaction conditions has been developed. 4-CN-pyridine was found to be a new and effective cyanation reagent under catalyst-free conditions. Mechanistic studies support a nucleophilic reaction pathway, and the cyanation protocol can be applied to diverse substrates including N,N-dialkyl aniline and indole derivatives.

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U2 - 10.1021/acs.orglett.2c01897

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SN - 1523-7060

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EP - 6363

JO - Organic Letters

JF - Organic Letters

IS - 35

ER -

Paired Electrolysis for Decarboxylative Cyanation: 4-CN-Pyridine, a Versatile Nitrile Source

Abstract

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