Regioselective difunctionalization of pyridines via 3,4-pyridynes?
Chemical Science Pub Date: 2021-03-25 DOI: 10.1039/D1SC01208H
Abstract
A new regioselective 3,4-difunctionalization of 3-chloropyridines via 3,4-pyridyne intermediates is reported. Regioselective lithiation of 3-chloro-2-ethoxypyridine and a related 2-thio-derivative followed by treatment with aryl- and alkylmagnesium halides as well as magnesium thiolates at ?78 °C produced 3,4-pyridynes during heating to 75 °C. Regioselective addition of the Grignard moiety in position 4 followed by an electrophilic quench in position 3 led to various 2,3,4-trisubstituted pyridines. This method was adapted into a continuous flow set-up. As an application, we have prepared a key intermediate for (±)-paroxetine.
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Journal Name：Chemical Science
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CAS no.: 89640-58-4
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