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CC BY-NC-ND 4.0 · SynOpen 2020; 04(04): 123-131
DOI: 10.1055/s-0040-1706004
DOI: 10.1055/s-0040-1706004
paper
Traceless Redox-Annulations of Alicyclic Amines
Financial support from the NIH–NIGMS (Grant R01GM101389) is gratefully acknowledged. We further acknowledge the National Science Foundation (grant # 1828064 to K.A.A.) and the University of Florida for funding the purchase of the X-ray equipment.
Abstract
Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with ortho-(nitromethyl)benzaldehyde. Benzoic acid acts as a promoter in these reactions, which involve concurrent amine α-C–H bond and N–H bond functionalization. Subsequent removal of the nitro group provides access to tetrahydroprotoberberines not accessible via typical redox-annulations. Also reported are decarboxylative annulations of ortho-(nitromethyl)benzaldehyde with proline and pipecolic acid.
Key words
C–H bond functionalization - redox-neutral - redox-annulation - denitration - decarboxylative annulationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706004.
- Supporting Information
- CIF File
Publication History
Received: 12 November 2020
Accepted after revision: 04 December 2020
Article published online:
16 December 2020
© 2020. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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Selected recent reviews on amine C–H functionalization, including redox-neutral approaches:
Recent examples of mechanistically diverse amine C–H bond functionalization reactions:
Additional examples of amine redox-annulations:
For detailed discussions on the mechanisms of these transformations, see references:
Examples of redox-neutral α-C–H bond annulations of secondary amines that likely involve a pericyclic step:
Decarboxylative annulations:
Selected reviews on decarboxylative coupling reactions not limited to amino acids:
Starting material synthesis: