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Synthesis 1999; 1999(3): 503-514
DOI: 10.1055/s-1999-3426
DOI: 10.1055/s-1999-3426
feature article
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Functionalized Organolithium Compounds by DTBB-Catalyzed Sulfur-Lithium Exchange
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Publication History
Publication Date:
31 December 1999 (online)
The successive reaction of β- or γ-hydroxy or amino phenyl thioethers (1, 4) with butyllithium and an excess of lithium powder in the presence of a catalytic amount of DTBB in THF at - 78 °C leads to the formation of the corresponding β-γ-functionalized organolithium compounds 2 or 5, respectively, which by treatment with different electrophiles [D2O, t-BuCHO, PhCHO, Me2CO, (CH2)4CO, (CH2)5CO] at temperatures ranging between - 78 °C and room temperature yields, after hydrolysis with water, the expected functionalized alcohols or amines 3 or 6, respectively, in a completely regioselective manner.
lithiation - arene-catalysis - functionalization - organolithium