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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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Coupling Reactions of Anhydro-Aldose Tosylhydrazones with Boronic Acids

Tímea Kaszás¹, Balázs Áron Baráth¹, Bernadett Balázs¹

¹Department of Organic Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, Hungary.

Molecules (Basel, Switzerland)

|March 26, 2022

Abstract:

A catalyst-free coupling reaction between O-peracetylated, O-perbenzoylated, O-permethylated, and O-permethoxymethylated 2,6-anhydro-aldose tosylhydrazones (C-(β-d-glycopyranosyl)formaldehyde tosylhydrazones) and aromatic boronic acids is reported. The base-promoted reaction is operationally simple and exhibits a broad substrate scope. The main products in most of the transformations were open-chain 1-C-aryl-hept-1-enitol type compounds while the expected β-d-glycopyranosylmethyl arenes (benzyl C-glycosides) were formed in subordinate yields only. A mechanistic rationale is provided to explain how a complex substrate may change the well-established course of the reaction.

Keywords:

C-glycosides anhydro-aldose tosylhydrazones coupling heptenitols

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