Transient imines as ‘next generation’ directing groups for the catalytic functionalisation of C–H bonds in a single operation
File(s)
Accepted version
Author(s)
St John-Campbell, S
Bull, JA
Type
Journal Article
Abstract
C–H Functionalisation promises a paradigm shift in synthetic planning. However, the additional steps often required to install and remove directing groups currently detracts from the efficiency. The strategy of reversible installation of a directing group via an imine linkage has recently emerged, with the imine formed and hydrolysed in situ. Such transient directing groups can promote transition metal catalysed functionalisation of unactivated C–H bonds of aldehydes, ketones and amines. This approach removes additional steps usually required for covalent directing groups and can use catalytic quantities of the imine forming component. This review updates the rapidly developing field of transient directing groups for C–H functionalisation on sp2 and sp3 carbon centres, to form new C–C and C–X bonds. We focus on the structures of the transient directing groups as mono or bidentate coordinating groups for various metal catalysts.
Date Issued
2018-07-07
Date Acceptance
2018-05-18
Citation
Organic and Biomolecular Chemistry, 2018, 16 (25), pp.4582-4595
ISSN
1472-7781
Publisher
Royal Society of Chemistry
Start Page
4582
End Page
4595
Journal / Book Title
Organic and Biomolecular Chemistry
Volume
16
Issue
25
Copyright Statement
© 2018 The Royal Society of Chemistry.
Sponsor
Engineering & Physical Science Research Council (EPSRC)
The Royal Society
The Royal Society
Identifier
http://pubs.rsc.org/en/content/articlelanding/2014/OB/C8OB00926K#!divRelatedContent&articles
Grant Number
EP/J001538/1
UF140161
RG150444
Subjects
Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
UNACTIVATED C(SP(3))-H BONDS
CARBON-HYDROGEN BONDS
FREE PRIMARY AMINES
INTERMOLECULAR HYDROACYLATION
ALIPHATIC-AMINES
AROMATIC KETONES
DIRECT ARYLATION
ORTHO-ALKYLATION
DUAL ACTIVATION
ALDEHYDES
Organic Chemistry
0304 Medicinal and Biomolecular Chemistry
0305 Organic Chemistry
1115 Pharmacology and Pharmaceutical Sciences
Publication Status
Published
Date Publish Online
2018-05-18