Palladium-Catalyzed Amide N–C Hiyama Cross-Coupling: Synthesis of Ketones

N-Acylglutarimides and arylsiloxanes reacted in the presence of Pd­(OAc)2/PCy3, Et3N·3HF, and LiOAc to provide the corresponding arylketones in good yields. Aryl-, vinyl-, and alkyl-substituted N-acylglutarimides showed good activity in the coupling reactions of arylsiloxanes. The reaction had a bro...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2020-12, Vol.22 (23), p.9190-9195
Main Authors: Idris, Muhammad Aliyu, Lee, Sunwoo
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:N-Acylglutarimides and arylsiloxanes reacted in the presence of Pd­(OAc)2/PCy3, Et3N·3HF, and LiOAc to provide the corresponding arylketones in good yields. Aryl-, vinyl-, and alkyl-substituted N-acylglutarimides showed good activity in the coupling reactions of arylsiloxanes. The reaction had a broad substrate scope and showed good functional group tolerance. N-Benzoylsuccinimide and N-protected N-phenylbenzamides showed good activities in coupling reactions with phenylsiloxane. The employment of CuF2 as an activor afforded the decarbonylative products at 160 °C.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03260