Nickel-Catalyzed, para-Selective, Radical-Based Alkylation of Aromatic Ketones

A direct, para-selective, radical-based alkylation of aromatic ketones with alkanes has been developed using a nickel catalyst with oxamide as the ligand. Acetophenones bearing electron-withdrawing substituents were functionalized directly with simple alkanes with high para-selectivity while acetoph...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2020-02, Vol.22 (3), p.854-857
Main Authors: Wang, Jie, Pang, Yu-Bo, Tao, Na, Zeng, Runsheng, Zhao, Yingsheng
Format: Article
Language:English
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:A direct, para-selective, radical-based alkylation of aromatic ketones with alkanes has been developed using a nickel catalyst with oxamide as the ligand. Acetophenones bearing electron-withdrawing substituents were functionalized directly with simple alkanes with high para-selectivity while acetophenones with electron-donating groups were mainly para-functionalized. A mechanistic study indicated that C–H bond activation of the aromatic ring may be the rate-determining step of the reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b04327