The reaction of 2,3-benzofuran (1) with lithium and a catalytic amount of 4,4Ј-di-tert-butylbiphenyl (TDBB, 5 mol %) in THF at 0°C leads to the stereoselective ring opening of the heterocycle, yielding the (Z)-organolithium derivatives (2) which, by reaction with different electrophiles [H 2 O, D 2 O, tBuCHO, PhCHO, Ph(CH 2 ) 2 CHO, Me 2 CO, nPrCOMe,
The DTBB-catalyzed lithiation of 4-hetero-substituted dibenzothiins (phenoxathiin, phenothiazine, and thianthrene) gives the corresponding functionalized organolithium intermediates, which by reaction with different electrophiles afford the expected functionalized thiols. The cyclization of some alcohol compound derivatives gives the corresponding homologous seven-membered dibenzo heterocycles.
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