Subsequently, we explored the versatility of various phosphonium salts with aldehydes and ketones (Figure ). We selected piperonal as a model aldehyde substrate due to the benzodioxole motif's frequent presence in pharmaceutically active compounds and promising drug candidates. Generally, reactions with non-stabilized and semi-stabilized ylides (yielding products 28-33, 37, 38) gave mixtures of isomers, as expected. Stabilized ylides (yielding products 34-36) exclusively gave the E-isomers in yields ranging from 68% to 92%. Some substrates required slightly longer milling times due to increased steric hindrance affecting reaction rates as the substitution on the Wittig reagent increased, but no reaction was conducted for longer than 1 hour. Deuteromethenylation using PPh₃CD₃I was feasible under the given reaction conditions, yielding deuterovinylated products 27 and 39 in 81% and 90%, respectively. Remarkably, this protocol allowed for the introduction of several valuable functional groups via the respective phosphonium salts: Weinreb amide (36 and 47), dioxolane (37), ester (35 and 46), and nitrile derivative (38). This versatility underscores the method's broad applicability and potential for generating a wide array of functionalized products.