Transition metal free reductive hydroxymethylation of isoquinolines
| Autor: | Timothy J. Donohoe, Alexandru Grozavu, Peter J. Lindsay-Scott, Hamish B. Hepburn, Benjamin M. Reeves |
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| Rok vydání: | 2019 |
| Předmět: |
transition-metal-free synthesis
Tandem Tetrahydroisoquinoline 010405 organic chemistry Communication General Chemistry General Medicine 010402 general chemistry Combinatorial chemistry 01 natural sciences Catalysis Communications 0104 chemical sciences chemistry.chemical_compound Cascade reaction chemistry Transition metal Deuterium Labelling Transition‐Metal‐Free Synthesis formaldehyde reductive-functionalization tandem reaction Potential mechanism tetrahydroisoquinoline |
| Zdroj: | Angewandte Chemie (International Ed. in English) Angewandte Chemie International Edition |
| ISSN: | 1521-3773 |
| Popis: | A transition‐metal‐free reductive hydroxymethylation reaction has been developed, enabling the preparation of tetrahydroisoquinolines bearing C4‐quaternary centers from the corresponding isoquinolines. Deuterium labelling studies and control experiments enable a potential mechanism to be elucidated which features a key Cannizzaro‐type reduction followed by an Evans–Tishchenko reaction. When isoquinolines featuring a proton at the 4‐position are used, a tandem methylation‐hydroxymethylation occurs, leading to the formation of 2 new C−C bonds in one pot. Reductive Functionalization: The transition‐metal‐free synthesis of tetrahydroisoquinolines that bear a quaternary center through a reductive hydroxymethylation process is reported. It is a simple and robust method using cheap and accessible reagents to prepare complex heterocyclic motifs. |
| Databáze: | OpenAIRE |
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