N-Boc-α-Diazo Glutarimide as Efficient Reagent for Assembling N-Heterocycle-Glutarimide Diads via Rh(II)-Catalyzed N-H Insertion Reaction

Submitting author affiliation:
Saint Petersburg State University, Saint Petersburg, Russian Federation

Beilstein Arch. 2023, 202341. https://doi.org/10.3762/bxiv.2023.41.v1

Published 05 Oct 2023

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A technique has been proposed for incorporating a heterocyclic component into a glutarimide framework employing Rh2(esp)2-catalysed N-H insertion with the involvement of N-Boc-α-diazo glutarimide. The new diazo reagent is more stable, soluble and convenient to prepare than the previously suggested one. The approach permits the application of diverse heterocycles, including both aromatic and saturated NH-substrates. This yields structures that are appealing for generating Cereblon ubiquitin-ligase ligands and for potential use in crafting PROTAC molecules.

Keywords: diazocarbonyl compounds, Rh(II)-catalysis, NH insertion reaction, N-heterocycles, CRBN ligands

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Kantin, G.; Golubev, P.; Sapegin, A.; Bunev, A.; Dar'in, D. Beilstein Arch. 2023, 202341. doi:10.3762/bxiv.2023.41.v1

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