Work

Solid-Phase Synthesis of s-Tetrazines

Year: 2023

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide An efficient synthesis of s -tetrazines by solid-phase methods is described. This synthesis route was compatible with different solid-phase resins and linkers and did not require metal catalysts or high temperatures. Monosubstituted tetrazines were routinely synthesized using thiol-promoted chemistry, using dichloromethane as a carbon source, while disubstituted unsymmetrical aryl or alkyl tetrazines were synthesized using readily available nitriles. This efficient approach enabled the synthesis of s -tetrazines in high yields (70–94%), eliminating the classical solution-phase problems of mixtures of symmetrical and unsymmetrical tetrazines, with only a single final purification step required, and paves the way to the rapid synthesis of s -tetrazines with various applications in bioorthogonal chemistry and beyond.

Source: Organic Letters

DOI: 10.1021/acs.orglett.3c00955

Authors: Zainab S. Alghamdi, Maxime Klausen, Alessia Gambardella, Annamaria Lilienkampf, Mark Bradley

Institutions: Imam Abdulrahman Bin Faisal University, University of Edinburgh

Language: English

Topic: Click Chemistry and Applications

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,000

Funders: Ministry of Education – Kingdom of Saudi Arabi, Imam Abdulrahman Bin Faisal University