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.
Highlights
N-Tosylhydrazones have extensively been used in organic synthesis for more than half a century
In the past decade N-tosylhydrazones were generally applied in a variety of carbon–carbon and carbon–heteroatom bond forming reactions [1–6]
We began a systematic study aimed at the investigation of the applicability of anhydro-aldosetosylhydrazones 1 [7–9] in coupling reactions
Summary
N-Tosylhydrazones have extensively been used in organic synthesis for more than half a century. In the past decade N-tosylhydrazones were generally applied in a variety of carbon–carbon and carbon–heteroatom bond forming reactions [1–6]. These transition metal catalyzed or catalyst-free cross-coupling reactions proceed through the in situ generated diazo compounds, followed by the formation of metal–carbene or carbene intermediates, which lead to the corresponding coupled products. Carbohydrate tosylhydrazones are known, but their application in coupling reactions is poorly investigated. We began a systematic study aimed at the investigation of the applicability of anhydro-aldosetosylhydrazones 1 [7–9] in coupling reactions. In this project C-O [10], C-S [11], and C-N [12]
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