ortho‐Acylation of Aryl Iodides Enabled with Imides via Palladium/Norbornene/CuI Catalysis

Herein, a three component Catellani‐type reaction catalyzed by the Palladium/Norbornene/CuI (Pd/NBE/CuI) cooperative system by using N‐acylph‐thalimides as acyl electrophiles is reported, which gives access to a series of aromatic ketones. The transformation is performable in the presence of water,...

Full description

Saved in:
Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 364; no. 20; pp. 3506 - 3511
Main Authors Zhao, Shen, Yang, Shimin, Du, Guopeng, Zhang, Daopeng, Liu, Hui, Sun, Feng‐Gang
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 18.10.2022
Wiley Subscription Services, Inc
Subjects
Acylation
Alkenes
Aromatic compounds
Catellani reaction
Chemistry
Chemistry, Applied
Chemistry, Organic
C−C coupling
C−H activation
Imide
Imides
Iodides
Ketones
Multicomponent reactions
Palladium
Physical Sciences
Reagents
Science & Technology
Substrates
C-C coupling
FRIEDEL-CRAFTS ACYLATION
DOMINO REACTION
HALIDES
REAGENTS
Catellani reaction
O-TERARYLS
EFFICIENT SYNTHESIS
CLEAVAGE
FUNCTIONALIZATION
Imide
Multicomponent reactions
C-H activation
BOND
Acylation
Online AccessGet full text

Cover

More Information
Summary:Herein, a three component Catellani‐type reaction catalyzed by the Palladium/Norbornene/CuI (Pd/NBE/CuI) cooperative system by using N‐acylph‐thalimides as acyl electrophiles is reported, which gives access to a series of aromatic ketones. The transformation is performable in the presence of water, albeit with decreased reaction yield. The additive CuI was crucial to facilitate the cleavage of C(O)−N bond of imide. This protocol showed broad substrate scope: both alkyl and aryl acyl groups could be installed at the ortho‐position of aryl iodides; alkenes and boronic acids can be used as termination reagents.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202200801