Unusual tBuLi Induced Ortholithiation versus Halogen?Lithium Exchange in Bromopyridines: Two Alternative Strategies for Functionalization.

Abstract : The reaction of lithiating agents with various 3-bro-mopyridines has been investigated. An unprecedented selectivity was observed with t-BuLi, which effected a clean lithiation at C-4. With 3-bromo and 2-chloro-3-bromo pyridines, the ortholithiation-exchange ratio was strongly electrophile and addition order dependent while 2-chloro-5-bromopyridine always gave exclusive C-4 substitution.
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https://hal.univ-lorraine.fr/hal-01998669
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Submitted on : Wednesday, March 20, 2019 - 9:31:53 PM
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Philippe Pierrat, Philippe Gros, Yves Fort. Unusual tBuLi Induced Ortholithiation versus Halogen?Lithium Exchange in Bromopyridines: Two Alternative Strategies for Functionalization.. SYNLETT, Georg Thieme Verlag, 2005, pp.2319-2322. ⟨10.1055/s-2004-831337⟩. ⟨hal-01998669⟩

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