Aryl radical cyclization with alkyne followed by tandem carboxylation in methyl 4-tert-butylbenzoate-mediated electrochemical reduction of 2-(2-propynyloxy)bromobenzenes in the presence of carbon dioxide
| Autor: | Asahi Katayama, Shoji Hara, Hisanori Senboku |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
Aryl radical 010405 organic chemistry Chemistry Organic Chemistry Indane Alkyne 010402 general chemistry 01 natural sciences Biochemistry Radical cyclization Medicinal chemistry 0104 chemical sciences Bromobenzenes chemistry.chemical_compound Carboxylation Succinic acid Drug Discovery Indoline Organic chemistry |
| Zdroj: | Tetrahedron. 72:4626-4636 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2016.06.032 |
| Popis: | Constant current electrolysis of 2-(2-propynyloxy)bromobenzenes in DMF using an undivided cell equipped with a Pt cathode and an Mg anode in the presence of carbon dioxide and an electron transfer mediator, methyl 4-tert-butylbenzoate, resulted in aryl radical cyclization with a carbon–carbon triple bond followed by fixation of two molecules of carbon dioxide to give 2,2-ring-fused succinic acid derivatives in moderate to good yields. Dihydrobenzofuran, indoline, dihydrobenzothiophene, and indane as well as tetrahydropyran skeletons were successfully constructed by aryl radical cyclization, and unique tandem carboxylation successively occurred to produce succinic acids. One of the resulting succinic acid derivatives, 3-carboxy-2,3-dihydrobenzofuran-3-ylacetic acid, was successfully applied to the synthesis of a novel spiro compound consisting of 2,3-dihydrobenzofuran and γ-butyrolactone at each C3 position in two steps in high yield. |
| Databáze: | OpenAIRE |
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