The "cesium effect" magnified: exceptional chemoselectivity in cesium ion mediated nucleophilic reactions.

ABSTRACT: Chemodivergent construction of structurally distinct heterocycles from the same precursors by adjusting specific reaction parameters is an emergent area of organic synthesis; yet, understanding of the processes that underpin the reaction divergence is lacking, preventing the development of new synthetic methods by systematically harnessing key mechanistic effects. We describe herein cesium carbonate-promoted oxadiaza excision cross-coupling reactions of β-ketoesters with 1,2,3-triazine 1-oxides that form pyridones in good to high yields, instead of the sole formation of pyridines when the same reaction is performed in the presence of other alkali metal carbonates or organic bases. The reaction can be further extended to the construction of synthetically challenging pyridylpyridones. A comp

SUBMITTER: Biswas S 

PROVIDER: S-EPMC10988617 | biostudies-literature | 2024 Apr

REPOSITORIES: biostudies-literature