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The silver‐promoted reaction of tertiary cyclobutanols with N‐methoxypyridinium salts enables the efficient synthesis of a range of C2‐substituted pyridines. The overall process likely occurs by ring‐opening (via β‐scission) of the cyclobutoxy radical to generate the corresponding γ‐keto alkyl radical that itself adds to the pyridinium salt. A wide range of tertiary cyclobutanols and N‐methoxypyridinium...