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 3月 2023
Accepted
30 3月 2023
First published
30 3月 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements