Issue 9, 2023

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

Abstract

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 H2O-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.

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

Supplementary files

Article information

Article type
Paper
Submitted
03 mrt 2023
Accepted
30 mrt 2023
First published
30 mrt 2023

Green Chem., 2023,25, 3543-3548

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

Z. Zhang, Z. Hou, H. Chen, P. Li and L. Wang, Green Chem., 2023, 25, 3543 DOI: 10.1039/D3GC00728F

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