Science· 2026Q1
Embracing triplet nitrenes for C-to-N replacement of complex bicyclic (hetero)aryl azides
- 5citations
- Q1SCImago
- 2026year
Short summary
A new reaction productively engages triplet aryl nitrenes for carbon-to-nitrogen replacement on bicyclic heteroarenes, overcoming limitations of previous methods.
AI-generated from the title and abstract; the full text is not read.
Key points
- Reports a reaction that productively engages triplet aryl nitrenes for C-to-N replacement.
- Successfully applies the reaction to a range of bicyclic heteroarenes including naphthalenes, indoles, and benzofurans.
- The reaction proceeds under mild conditions, enabling application to complex, sensitive natural products.
- Overcomes limitations of prior C-to-N replacement methods that were substrate-specific and relied on harsh oxidation.
AI-generated from the title and abstract; the full text is not read.
Abstract
Despite recent proof-of-concept advances, aromatic carbon-to-nitrogen replacement reactions remain substrate specific and exhibit an overreliance on harsh oxidation methods that preclude their deployment in demanding contexts. Transformations relying on singlet nitrene valence isomerization, in particular, have suffered from competitive intersystem crossing to the triplet spin state, which does not undergo the same rearrangement. In this work, we report a reaction that productively engages triplet aryl nitrenes for carbon-to-nitrogen replacement on the benzenoid ring of a range of bicyclic heteroarenes, including naphthalenes, anthracene, indoles, benzofurans, benzothiophene, indazoles, and benzisothiazoles. The reaction proceeds under mild conditions, which enables its application to complex, sensitive natural products.
The authors' abstract, as published at the source. Science, 2026 · DOI ↗
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Field: Physical and Theoretical Chemistry
Physical and Theoretical ChemistryChemistry