Late stage C-H functionalization via chalcogen and pnictogen salts

Late-stage functionalization (LSF) of heteroarenes can dramatically accelerate SAR studies by enabling the installation of functional groups that would otherwise complicate a synthetic sequence. Although heteroaryl halides and boronic esters have well-established chemistries for LSF, alternatives th...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2020-09, Vol.11 (37), p.10047-10060
Main Authors: Kelly, Christopher B, Padilla-Salinas, Rosaura
Format: Article
Language:English
Subjects:
Chemistry
Esters
Functional groups
Halides
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Summary:Late-stage functionalization (LSF) of heteroarenes can dramatically accelerate SAR studies by enabling the installation of functional groups that would otherwise complicate a synthetic sequence. Although heteroaryl halides and boronic esters have well-established chemistries for LSF, alternatives that enable site-selective C-H functionalization are highly attractive. Recently, three unrelated cationic groups (phosphonium, pyridinium, and thianthrenium), which can replace C-H bonds late stage, have been identified as precursors to various functional groups. This review will discuss the synthesis and application of these three salts with an emphasis on their use for LSF and application to medicinal chemistry.
ISSN:2041-6520
2041-6539
DOI:10.1039/d0sc03833d