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Silver-Promoted Radical Ring-Opening/Pyridylation of Cyclobutanols with N-Methoxypyridinium Salts |
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| Authors: | Yu Chen Guang-Yi Zhang Chan Guo Dr. Ping Lan Prof. Dr. Martin G. Banwell Dr. Yu-Tao He |
| Affiliation: | 1. Institute for Advanced and Applied Chemical Synthesis, Jinan University, Guangzhou, 510632 Guangdong, P. R. China College of Pharmacy, Jinan University, Guangzhou, 510632 Guangdong, P. R. China These authors contributed equally to this work;2. Institute for Advanced and Applied Chemical Synthesis, Jinan University, Guangzhou, 510632 Guangdong, P. R. China College of Pharmacy, Jinan University, Guangzhou, 510632 Guangdong, P. R. China;3. Institute for Advanced and Applied Chemical Synthesis, Jinan University, Guangzhou, 510632 Guangdong, P. R. China |
| Abstract: | 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 salts are compatible with the reaction conditions. |
| Keywords: | Cyclobutanols silver N-methoxypyridinium salts β-scission γ-pyridylated ketones |