Details

Autor(en) / Beteiligte

• Zhang, Zhongyi
• Hou, Zhong-Wei
• Chen, Hao
• Li, Pinhua
• Wang, Lei

Titel

Electrochemical electrophilic bromination/spirocyclization of N -benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes

Ist Teil von

• Green chemistry : an international journal and green chemistry resource : GC, 2023-05, Vol.25 (9), p.3543-3548

Ort / Verlag

Cambridge: Royal Society of Chemistry

Erscheinungsjahr

2023

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• An electrochemical electrophilic bromination/spirocyclization of N -benzyl-acrylamides with 2-bromoethan-1-ol as the brominating reagent has been developed. The paired electrolysis employs low concentrations of bromine produced from both cathodic reduction and anodic oxidation as an electrophile, and realizes an H 2 O-involved electrophilic spirocyclization. A number of unexplored brominated 2-azaspiro[4.5]decanes are obtained with satisfactory yields under mild conditions, and the reaction exhibits good efficiency at the gram-scale synthesis. In addition, this approach is further highlighted by late-stage transformations and synthetic applications in constructing cyclohepta[ c ]pyrrole-1,6-diones via debromination tandem cyclization of brominated 2-azaspiro[4.5]decanes.