Poorly available 5-iodo-and 5-bromoindolizines were prepared via regioselective lithiation of indolizines followed by halogenation. 5-Halogenoindolizines were found to be passive toward nucleophiles, whereas they may be trifluoroacetylated at C-3 and involved in reaction with DMAD giving cycl [3.2. 2] azine. The first successful Suzuki-coupling of 5- bromo (iodo) indolizines with different arylboronic acids (performed as a parallel synthesis ...