Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 44, Pages 15697-15701Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908857
Keywords
formaldehyde; reductive-functionalization; tandem reaction; tetrahydroisoquinoline; transition-metal-free synthesis
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Funding
- EPSRC [EP/L023121/1]
- European Commission for a Marie Sklodowska-Curie Actions fellowship [792562 H2020-MSCA-IF-2017]
- EPSRC [EP/L023121/1] Funding Source: UKRI
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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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