Alumination of aryl methyl ethers: switching between sp
2
and sp
3
C–O bond functionalisation with Pd-catalysis
2
and sp
3
C–O bond functionalisation with Pd-catalysis
File(s)d1cc05408b.pdf (2.16 MB)
Published version
Author(s)
Type
Journal Article
Abstract
The reaction of [{(ArNCMe)2CH}Al] (Ar = 2,6-di-iso-propylphenyl) with aryl methyl ethers proceeded with alumination of the sp3 C–O bond. The selectivity of this reaction could be switched by inclusion of a catalyst. In the presence of [Pd(PCy3)2], chemoselective sp2 C–O bond functionalisation was observed. Kinetic isotope experiments and DFT calculations support a catalytic pathway involving the ligand-assisted oxidative addition of the sp2 C–O bond to a Pd–Al intermetallic complex.
Date Acceptance
2021-10-12
Citation
Chemical Communications, - (88), pp.1-4
ISSN
1359-7345
Publisher
Royal Society of Chemistry (RSC)
Start Page
1
End Page
4
Journal / Book Title
Chemical Communications
Volume
-
Issue
88
Copyright Statement
© The Royal Society of Chemistry 2021. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.
License URL
Sponsor
Engineering & Physical Science Research Council (EPSRC)
Commission of the European Communities
Identifier
https://pubs.rsc.org/en/content/articlelanding/2021/CC/D1CC05408B
Grant Number
EP/L011514/1
677367
Subjects
Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
CARBON-OXYGEN
OXIDATIVE ADDITION
ALUMINUM(I)
BORYLATION
ACTIVATION
LIGNIN
SILYLATION
ALKYLATION
RHODIUM(I)
CONVERSION
Organic Chemistry
03 Chemical Sciences
Publication Status
Published online
Date Publish Online
2021-10-12