Core-Regenerating Atom-Pair Exchange Enables Skeletal Carbon Isotope Incorporation into Pyridines.
- 1Department of Chemistry, Iowa State University, Ames, Iowa50011, United States.
Abstract
We report a core-regenerating atom pair exchange strategy for skeletal carbon isotope incorporation into pyridines. The two-step sequence proceeds through pyridine dearomatization followed by a [4 + 2]/retro-[4 + 2] cycloaddition cascade with an isotope-labeled sulfonyl cyanide reagent, enabling selective replacement of a pyridine carbon atom with an isotopically labeled counterpart. This transformation addresses a longstanding challenge in the preparation of carbon-isotope-labeled pyridines, which are valuable for medicinal chemistry and ADMET (absorption, distribution, metabolism, excretion, and toxicity) studies. The method exhibits high regioselectivity and broad tolerance of diverse pyridine substitution patterns, providing rapid access to a wide range of 13C-labeled pyridine building blocks and bioactive molecules.
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BibTeX
@article{han2026coreregenerating,
title = {{Core-Regenerating Atom-Pair Exchange Enables Skeletal Carbon Isotope Incorporation into Pyridines.}},
author = {Jingqiang Han and Erin A Jacobsen and Yu-An Zhang},
journal = {Journal of the American Chemical Society},
year = {2026},
month = sep,
doi = {10.1021/jacs.6c11666},
url = {https://europepmc.org/article/MED/42915556},
note = {CC BY-NC-ND},
}
RIS
TY - JOUR
TI - Core-Regenerating Atom-Pair Exchange Enables Skeletal Carbon Isotope Incorporation into Pyridines.
AU - Jingqiang Han
AU - Erin A Jacobsen
AU - Yu-An Zhang
PY - 2026
DA - 2026/09/01
JO - Journal of the American Chemical Society
DO - 10.1021/jacs.6c11666
UR - https://europepmc.org/article/MED/42915556
AB - We report a core-regenerating atom pair exchange strategy for skeletal carbon isotope incorporation into pyridines. The two-step sequence proceeds through pyridine dearomatization followed by a [4 + 2]/retro-[4 + 2] cycloaddition cascade with an isotope-labeled sulfonyl cyanide reagent, enabling selective replacement of a pyridine carbon atom with an isotopically labeled counterpart. This transformation addresses a longstanding challenge in the preparation of carbon-isotope-labeled pyridines, which are valuable for medicinal chemistry and ADMET (absorption, distribution, metabolism, excretion, and toxicity) studies. The method exhibits high regioselectivity and broad tolerance of diverse pyridine substitution patterns, providing rapid access to a wide range of 13C-labeled pyridine building blocks and bioactive molecules.
SN - 0002-7863
SN - 1520-5126
ER -