Oxidative coupling of tetraalkynyltin with aldehydes leading to alkynyl ketones

The reaction of tetraalkynyltin with aldehydes was studied for the first time. The reaction was shown to proceed as a tandem process of nucleophilic addition of tin acetylide to aldehyde followed by Oppenauer-type oxidation of produced tin alcoholates, and may be used as a convenient one-pot approach to acetylenic ketones. The advantages and limitations of the proposed method are discussed. © 2017 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.