Issue 8, 2021

Ruthenium catalyzed β-selective alkylation of vinylpyridines with aldehydes/ketones via N2H4 mediated deoxygenative couplings

Abstract

Umpolung (polarity reversal) tactics of aldehydes/ketones have greatly broadened carbonyl chemistry by enabling transformations with electrophilic reagents and deoxygenative functionalizations. Herein, we report the first ruthenium-catalyzed β-selective alkylation of vinylpyridines with both naturally abundant aromatic and aliphatic aldehyde/ketones via N2H4 mediated deoxygenative couplings. Compared with one-electron umpolung of carbonyls to alcohols, this two-electron umpolung strategy realized reductive deoxygenation targets, which were not only applicable to the regioselective alkylation of a broad range of 2/4-alkene substituted pyridines, but also amenable to challenging 3-vinyl and steric-embedded internal pyridines as well as their analogous heterocyclic structures.

Graphical abstract: Ruthenium catalyzed β-selective alkylation of vinylpyridines with aldehydes/ketones via N2H4 mediated deoxygenative couplings

Supplementary files

Article information

Article type
Edge Article
Submitted
01 Dec 2020
Accepted
30 Dec 2020
First published
30 Dec 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 2870-2875

Ruthenium catalyzed β-selective alkylation of vinylpyridines with aldehydes/ketones via N2H4 mediated deoxygenative couplings

L. Lv and C. Li, Chem. Sci., 2021, 12, 2870 DOI: 10.1039/D0SC06586B

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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