A one-pot Suzuki-hydrogenolysis protocol for the modular synthesis of 2,5-diaryltetrazoles

Keith Livingstone; Sophie Bertrand; Craig Jamieson

doi:10.1021/acs.joc.0c00807

A one-pot Suzuki-hydrogenolysis protocol for the modular synthesis of 2,5-diaryltetrazoles

Keith Livingstone, Sophie Bertrand, Craig Jamieson

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Abstract

2,5-Diaryltetrazoles are a diverse range of compounds of considerable interest within the field of photochemistry as a valuable precursor of the nitrile imine 1,3-dipole. Current literature approaches toward this heterocycle remain unsuitable for the practical synthesis of a library of these derivatives. Herein, we disclose the development of a modular approach toward 2,5-diaryltetrazoles compatible with an array-type protocol, facilitated by a tandem Suzuki-hydrogenolysis approach.

Original language	English
Pages (from-to)	7413-7423
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	85
Issue number	11
Early online date	21 May 2020
DOIs	https://doi.org/10.1021/acs.joc.0c00807
Publication status	E-pub ahead of print - 21 May 2020

Keywords

2,5-diaryltetrazoles
photochemistry
modular approach

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10.1021/acs.joc.0c00807Licence: CC BY 4.0

Livingstone-etal-JOC-2020-A-one-pot-Suzuki-hydrogenolysis-protocol-for-the-modular-synthesisFinal published version, 1.9 MBLicence: CC BY 4.0

1 Finished

Industrial Case Account 2016 | Livingstone, Keith
Jamieson, C., Tomkinson, N. & Livingstone, K.
EPSRC (Engineering and Physical Sciences Research Council)
1/10/16 → 26/08/20
Project: Research Studentship Case - Internally allocated

Cite this

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abstract = "2,5-Diaryltetrazoles are a diverse range of compounds of considerable interest within the field of photochemistry as a valuable precursor of the nitrile imine 1,3-dipole. Current literature approaches toward this heterocycle remain unsuitable for the practical synthesis of a library of these derivatives. Herein, we disclose the development of a modular approach toward 2,5-diaryltetrazoles compatible with an array-type protocol, facilitated by a tandem Suzuki-hydrogenolysis approach.",

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AU - Livingstone, Keith

AU - Bertrand, Sophie

AU - Jamieson, Craig

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Y1 - 2020/5/21

N2 - 2,5-Diaryltetrazoles are a diverse range of compounds of considerable interest within the field of photochemistry as a valuable precursor of the nitrile imine 1,3-dipole. Current literature approaches toward this heterocycle remain unsuitable for the practical synthesis of a library of these derivatives. Herein, we disclose the development of a modular approach toward 2,5-diaryltetrazoles compatible with an array-type protocol, facilitated by a tandem Suzuki-hydrogenolysis approach.

AB - 2,5-Diaryltetrazoles are a diverse range of compounds of considerable interest within the field of photochemistry as a valuable precursor of the nitrile imine 1,3-dipole. Current literature approaches toward this heterocycle remain unsuitable for the practical synthesis of a library of these derivatives. Herein, we disclose the development of a modular approach toward 2,5-diaryltetrazoles compatible with an array-type protocol, facilitated by a tandem Suzuki-hydrogenolysis approach.

KW - 2,5-diaryltetrazoles

KW - photochemistry

KW - modular approach

U2 - 10.1021/acs.joc.0c00807

DO - 10.1021/acs.joc.0c00807

M3 - Article

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 11

ER -

A one-pot Suzuki-hydrogenolysis protocol for the modular synthesis of 2,5-diaryltetrazoles

Abstract

Keywords

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Industrial Case Account 2016 | Livingstone, Keith

Cite this