posted on 2012-09-07, 00:00authored byBartolo Gabriele, Raffaella Mancuso, Giuseppe Salerno, Richard C. Larock
A novel approach to 3-iodothiophenes by direct iodocyclization
of alkynylthiol derivatives is presented. A variety of 1-mercapto-3-yn-2-ols 5 (readily available from alkynylation of the corresponding
alpha-mercapto ketones or alpha-mercapto esters) were smoothly converted
into the corresponding 3-iodothiophene derivatives 6 in
good yields by reaction with molecular iodine in the presence of NaHCO3 at room temperature in MeCN as the solvent.