Síntese de benzamidas N-(3-Organocalcogenil)-2-propinílicas mediada por cul

Abstract

This work describes the study and development of an efficient methodology to the synthesis of N-(3-(organochalcogenyl)prop-2-yn-1-yl)amides via copper iodidecatalyzed cross-coupling reactions of propargylic amides and diorganyl dichalcogenides, using DMSO as solvent at room temperature, under ambient atmosphere (open flask). The generality of the catalytic system was tested by employing different diorganyl dichalcogenides, including diselenides, ditellurides e disulfides as well as differently substituted propargylic amides. Through this method, it became possible the synthesis of range of N-(3-(organochalcogenyl)prop-2-yn-1- yl)amides (19 examples) in 42 to 87% yields. Moreover, in order to evaluate the synthetic applicability of the obtained compounds, we have explored the potential of the carbon-chalcogen bond as reactive site in palladium-catalyzed Suzuki and Sonogashira type coupling reactions. Through these experiments we were able to obtain new molecules (4 examples) aryl and alkynyl groups bonded to the carbon sp of the propargylic amides in 54 to 82% yields