Installation of Minimal Tetrazines Through Silver-mediated Liebeskind-Srogl Coupling with Arylboronic Acids.

08:00 EDT 11th October 2019 | BioPortfolio

Summary of "Installation of Minimal Tetrazines Through Silver-mediated Liebeskind-Srogl Coupling with Arylboronic Acids."

Described is a general method for the installation of a minimal 6-methyltetrazin-3-yl group via the first example of a Ag-mediated Liebeskind-Srogl cross-coupling. The attachment of bioorthogonal tetrazines on complex molecules typically re-lies on linkers that can negatively impact the physiochemical properties of conjugates. Cross-coupling with arylboronic acids and a new reagent, 3-((p-biphenyl-4-ylmethyl)thio)-6-methyltetrazine (b-Tz), proceeds under mild, PdCl2(dppf)-catalyzed conditions to introduce minimal, linker-free te-trazine functionality. Safety considerations guided our design of b-Tz which can be prepared on decagram scale without han-dling hydrazine and without forming volatile, high-nitrogen tetrazine byproducts. Replacing conventional Cu(I) salts used in Liebeskind-Srogl cross-coupling with a Ag2O mediator resulted in higher yields across a broad library of aryl and het-eroaryl boronic acids and provides improved access to a fluorogenic tetrazine-BODIPY conjugate. A covalent probe for MAGL incorporating 6-methyltetrazinyl functionality was synthesized in high yield and labeled endogenous MAGL in live cells. This new reagent and Ag-mediated cross-coupling method is anticipated to find additional applications for di-rectly introducing the tetrazine subunit to complex substrates.


Journal Details

This article was published in the following journal.

Name: Journal of the American Chemical Society
ISSN: 1520-5126


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