Ligand-enabled ortho -C-H olefination of phenylacetic amides with unactivated alkenes

Although chelation-assisted C-H olefination has been intensely investigated, Pd(ii)-catalyzed C-H olefination reactions are largely restricted to acrylates and styrenes. Here we report a quinoline-derived ligand that enables the Pd(ii)-catalyzed olefination of the C(sp )-H bond with simple aliphatic...

Full description

Saved in:
Bibliographic Details
Published in:Chemical science (Cambridge) 2018-02, Vol.9 (5), p.1311-1316
Main Authors: Lu, Ming-Zhu, Chen, Xing-Rong, Xu, Hui, Dai, Hui-Xiong, Yu, Jin-Quan
Format: Article
Language:English
Subjects:
Acrylates
Aliphatic compounds
Alkenes
Alkylation
Amides
Catalysis
Chelation
Chemical reactions
Functional groups
Hydrogen bonds
Ligands
Quinoline
Styrenes
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Although chelation-assisted C-H olefination has been intensely investigated, Pd(ii)-catalyzed C-H olefination reactions are largely restricted to acrylates and styrenes. Here we report a quinoline-derived ligand that enables the Pd(ii)-catalyzed olefination of the C(sp )-H bond with simple aliphatic alkenes using a weakly coordinating monodentate amide auxiliary. Oxygen is used as the terminal oxidant with catalytic copper as the co-oxidant. A variety of functional groups in the aliphatic alkenes are tolerated. Upon hydrogenation, the -alkylated product can be accessed. The utility of this reaction is also demonstrated by the late-stage diversification of drug molecules.
ISSN:2041-6520
2041-6539
DOI:10.1039/c7sc04827k