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The deprotonation of 2-methoxypyridine was attempted using putative (TMP) 3 FeLi prepared from different iron sources. Using iodine to intercept the metalated 2-methoxypyridine, the best result was obtained from FeBr 2 (1equiv) using THF at room temperature; nevertheless, in addition to the expected iodide, the corresponding 2,2′-dimer was obtained (86% total yield). The origin of...
A series of chloro‐ and bromopyridines have been deprotometalated by using a range of 2,2,6,6‐tetramethylpiperidino‐based mixed lithium–metal combinations. Whereas lithium–zinc and lithium–cadmium bases afforded different mono‐ and diiodides after subsequent interception with iodine, complete regioselectivities were observed with the corresponding lithium–copper combination, as demonstrated by subsequent...
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