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Chemoselective lithiation of 6-chloro-1-halohex-1-ynes with lithium/naphthalene
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1  Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante (Spain)

Abstract: The reaction of different 6-chloro-1-halohex-1-ynes (1) with lithium naphthalene (1:2 molar ratio) and a carbonyl compound R1R2CO in THF at –78°C leads, after hydrolysis with water, to the corresponding chlorinated alcohols 2 through a selective lithiation of the sp carbon-halogen bond. The DTBB-catalysed lithiation of 6-chloro-1-halohexynes (1) in the presence of an excess of a carbonyl compound R1R2YCO as electrophile in THF at -78 ºC led, after hydrolysis with water, to diols 3.
Keywords: DTBB-catalysed lithiation, lithium-naphthalene, bromine-lithium exchange, chlorine-lithium exchange, electrophilic substitution, diols