44ª Reunião Anual Virtual da SBQ

α,β-unsaturated thioesters are valuable compound of biologically molecules that can be founded in all living organism, which is ubiquitous in biochemistry process. They are steadily gaining strong attention not only as an important biological active group, but also as an useful intermediate building block for new bond formation. Due their application in several areas, numerous methods for their preparation were developed, such as cycloaddition and olefinations. , However, many of these methods present regioselectivity problems and form complex mixture of products. In this context, Meyer-Schuster rearrangement became valuable alternative, as it favours the formation of α, β-unsaturated carbonyl compound. Recently, our research group applied the Meyer-Schuster rearrangement to transform propargyl thioalkyne in α-selanyl-α,β-unsaturated thioesters in presence of an electrophilic selenium species. Herein, we aim to explore the potential reactivity of propargyl thioalkyne for access α-iodo-α,β-unsaturated thioesters using halonium electrophilic species. Our preliminary study revealed that the employment of 5 mol % Ag2O at thioalkyne 1a, in CH3CN solvent, at room temperature (rt) and under inert environment, using N-iodosuccinimide (NIS) (1,5 equiv.), lead to formation of α-iodo-α,β-unsaturated thioesters in excellent yield (94 %). With the optimal reaction condition in hand, were synthesized 7 examples (2a-g) with good to excellent yields ranged from 52 to 94 %.