Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202302941
Keywords
C-H Functionalization; Dearomatization; Late-Stage Functionalization; meta-Selective; Pyridine
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The pyridine moiety is widely used in the synthesis of drugs, agrochemicals, catalysts, and functional materials. While direct functionalization of ortho- and para-positions is well-established, meta-selective pyridine C-H functionalization presents more challenges due to the inherent electronic properties of pyridines. In this review, we summarize the current methods for meta-C-H functionalization of pyridines, including the use of directing groups, non-directed metalation, and temporary dearomatization strategies. Recent advances in ligand control and temporary dearomatization are highlighted, while the advantages and limitations of these techniques are discussed, aiming to inspire further developments in this important area.
The pyridine moiety is an important core structure for a variety of drugs, agrochemicals, catalysts, and functional materials. Direct functionalization of C-H bonds in pyridines is a straightforward approach to access valuable substituted pyridines. Compared to the direct ortho- and para-functionalization, meta-selective pyridine C-H functionalization is far more challenging due to the inherent electronic properties of the pyridine entity. This review summarizes currently available methods for pyridine meta-C-H functionalization using a directing group, non-directed metalation, and temporary dearomatization strategies. Recent advances in ligand control and temporary dearomatization are highlighted. We analyze the advantages as well as limitations of current techniques and hope to inspire further developments in this important area.
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