Thioalkyltetrazines Synthesis from Aldehyde Precursors and Application in Ag-Mediated Liebeskind-Srogl…

Abstract

Tetrahydrotetrazines are readily prepared from aldehydes, but have minimal precedent as precursors to tetrazines of value to bioorthogonal chemistry applications. Formaldehyde and glyoxylate esters undergo condensation with ([1,1'-biphenyl]-4-ylmethyl)thiocarbohydrazide bromide to give practical access to new thioalkyltetrazines as crystalline solids. 3-(([1,1’-biphenyl]-4-ylmethyl)thio)-tetrazine (h-Tz) was used for the synthesis of monosubstituted tetrazines via silver-mediated Liebeskind-Srogl coupling. Tetrazine-3-carboxylic esters were also synthesized using this method, further expanding the library of functional tetrazines for bioorthogonal chemistry applications.

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BibTeX

@misc{jun2026thioalkyltetrazines,
  title = {{Thioalkyltetrazines Synthesis from Aldehyde Precursors and Application in Ag-Mediated Liebeskind-Srogl Coupling}},
  author = {HyunJune Jun and Chuanqi Wang and Stephanie Tsang and Remzi Duzguner and John D. Weaver and Shawn LaCasse and David W. Place and Christopher W. am Ende and Joseph M. Fox},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15009938/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009938/v1},
  note = {CC BY},
}

RIS

TY  - UNPB
TI  - Thioalkyltetrazines Synthesis from Aldehyde Precursors and Application in Ag-Mediated Liebeskind-Srogl Coupling
AU  - HyunJune Jun
AU  - Chuanqi Wang
AU  - Stephanie Tsang
AU  - Remzi Duzguner
AU  - John D. Weaver
AU  - Shawn LaCasse
AU  - David W. Place
AU  - Christopher W. am Ende
AU  - Joseph M. Fox
PY  - 2026
DA  - 2026/10/05
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15009938/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009938/v1
AB  - Tetrahydrotetrazines are readily prepared from aldehydes, but have minimal precedent as precursors to tetrazines of value to bioorthogonal chemistry applications. Formaldehyde and glyoxylate esters undergo condensation with ([1,1'-biphenyl]-4-ylmethyl)thiocarbohydrazide bromide to give practical access to new thioalkyltetrazines as crystalline solids. 3-(([1,1’-biphenyl]-4-ylmethyl)thio)-tetrazine (h-Tz) was used for the synthesis of monosubstituted tetrazines via silver-mediated Liebeskind-Srogl coupling. Tetrazine-3-carboxylic esters were also synthesized using this method, further expanding the library of functional tetrazines for bioorthogonal chemistry applications.
ER  -

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