Late-stage synthesis and application of photoreactive probes derived from direct benzoylation of heteroaromatic C-H bonds

A C-H functionalization strategy for the expedient access to photoreactive chemical probes of commonly found heterocyclic fragments or drug molecules of pharmaceutical relevance is described. A series of aryl glyoxylic acid reagents featuring pendant alkyne or azide clickable handles have been devel...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-05, Vol.18 (19), p.3669-3673
Main Authors: Hesp, Kevin D, Xiao, Jun, West, Graham M
Format: Article
Language:English
Subjects:
Alkynes
Aromatic compounds
Benzoylation
Chemical synthesis
Fragments
Glyoxylic acid
Probes
Reagents
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Summary:A C-H functionalization strategy for the expedient access to photoreactive chemical probes of commonly found heterocyclic fragments or drug molecules of pharmaceutical relevance is described. A series of aryl glyoxylic acid reagents featuring pendant alkyne or azide clickable handles have been developed for application in the radical-mediated appendage of benzoyl fragments onto simple heteroaromatic fragments, as well as more complex drug-like compounds. This unprecedented strategy of chemical probe synthesis allows for direct access to photoreactive chemical probes without any requirement of fragment pre-functionalization or significant synthetic re-evaluation. A synthetically-driven, late-stage C-H benzoylation strategy for the expedited preparation and evaluation of heterocyclic alternatives to more classical benzophenone photoreactive probes is reported.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob00336k