Article Synopsis
- Azine-containing biaryls, particularly those with pyridine rings, are important in chemistry, but their synthesis is often challenging due to the instability of 2-pyridine organometallics.
- Transition-metal-catalysed cross-coupling reactions are commonly used for synthesizing these compounds, but 2-pyridyl boron reagents face issues like poor reactivity in reactions like Suzuki-Miyaura.
- This Review highlights various methods for effectively coupling 2-pyridine nucleophiles with (hetero)aryl electrophiles, exploring both traditional and novel approaches to improve synthesis of unsymmetrical 2,2'-bis-pyridines.
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Article Abstract
Azine-containing biaryls are ubiquitous scaffolds in many areas of chemistry, and efficient methods for their synthesis are continually desired. Pyridine rings are prominent amongst these motifs. Transition-metal-catalysed cross-coupling reactions have been widely used for their synthesis and functionalisation as they often provide a swift and tuneable route to related biaryl scaffolds. However, 2-pyridine organometallics are capricious coupling partners and 2-pyridyl boron reagents in particular are notorious for their instability and poor reactivity in Suzuki-Miyaura cross-coupling reactions. The synthesis of pyridine-containing biaryls is therefore limited, and methods for the formation of unsymmetrical 2,2'-bis-pyridines are scarce. This Review focuses on the methods developed for the challenging coupling of 2-pyridine nucleophiles with (hetero)aryl electrophiles, and ranges from traditional cross-coupling processes to alternative nucleophilic reagents and novel main group approaches.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8246887 | PMC |
| http://dx.doi.org/10.1002/anie.202010631 | DOI Listing |
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