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Publications covering a new easy metal-free functionalization of pyridinoids (pyridines, quinolines, isoquinolines, acridine) under the action of the system of electron-deficient acetylenes (acetylenecarboxylic acid esters, acylacetylenes)/ P -nucleophiles (phosphine chalcogenides,  H -phosphonates) are reviewed. Special attention is focused on a S N  H  reaction of the regioselective cross-coupling of pyridines with secondary phosphine chalcogenides triggered by acylacetylenes to give 4-chalcogenophosphorylpyridines. In these processes, acetylenes act as three-modal adjuvants (i) activating the pyridine ring towards  P -nucleophiles, (ii) deprotonating the P-H bond and (iii) facilitating the nucleophilic addition of the  P -centered anion to a heterocyclic moiety followed by the release of the selectively reduced acetylenes ( E -alkenes).

Electron-Deficient Acetylenes as Three-Modal Adjuvants in SNH Reaction of Pyridinoids with Phosphorus Nucleophiles