With the optimized reaction conditions in hand, we evaluated the generality of this protocol by converting a diverse set of carbonyl compounds into their respective olefins (Figure ). Benzaldehyde derivatives (1 -9, 11, and 13) consistently yielded good to excellent results, ranging from 50% to 95%, regardless of their substitution patterns. Electron-donating (2, 3, 7 -9) and electron-withdrawing (5, 6, 13) groups, as well as combinations thereof (4), were well tolerated on various positions on the aromatic ring. Interestingly, under standard conditions without ylide pre-formation, product 9 was isolated in a moderate yield of 58%, with 16% of the dealkylated by-product N-methyl-4-vinylaniline. However, using the modified procedure with ylide pre-formation (1.2 equiv. of KO t Bu and 1.4 equiv. of PPh₃MeBr), the reaction proceeded smoothly, yielding product 9 in 80% with no observable dealkylation. A pinacol boronate-substituted aldehyde, which is highly useful for subsequent Suzuki-Miyaura coupling, reacted more reluctantly. But, after a prolonged milling time of 1 hour, the desired product 11 was obtained in 80% yield. This protocol is not limited to benzaldehyde derivatives; for example, 4-methoxycinnamaldehyde reacted smoothly, even on an increased scale, yielding product 12 in 84% (0.5 mmol scale) and 80% (2 mmol scale). Garner's aldehyde, a valuable chiral building block in natural product synthesis, underwent olefination readily, yielding 80% of its vinylated analogue 16. Notably, highly conjugated all-trans-retinal was methenylated in 71% yield (product 17), underscoring the potential of this method for future industrial applications in carotenoid synthesis. Beyond aldehydes, ketones also performed exceptionally well under the optimized reaction conditions (products 18-26). Cyclohexanone-derived substrates yielded products 18 (92%) and 21 (93%). Notably, the latter is highly base-sensitive, necessitating ylide pre-formation to ensure high yields. A pyridinyl moiety was readily tolerated (product 22), and natural product (-)-menthone, along with an adamantane-derived substrate, were converted to the vinylated products 23 and 24 in 71% and 89% yield, respectively. Remarkably, the complex steroid epiandrosterone was successfully converted to product 25, with the newly formed double bond positioned at C-17. Additionally, we demonstrated the feasibility of this approach for the late-stage olefination of the atypical antidepressant and nicotine antagonist Bupropion, yielding product 26 in 65%. This showcases the protocol's potential for application in the synthesis and late-stage functionalization of complex and bioactive molecules.