- Transition-Metal-Free Reductive Hydroxymethylation of Isoquinolines.
Transition-Metal-Free Reductive Hydroxymethylation of Isoquinolines.
Angewandte Chemie (International ed. in English) (2019-09-06)
Benjamin M Reeves, Hamish B Hepburn, Alexandru Grozavu, Peter J Lindsay-Scott, Timothy J Donohoe
PMID31486205
摘要
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.
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