Employing OTIPS OSF 2 in the deFS coupling led to cleavage of the TIPS group by the liberated fluoride anion, unmasking the phenol group of amino-oxetane products and providing a handle for divergent functionalization. The revealed phenol functionality of morpholine-oxetane 25 was readily alkylated (26, 27) or converted to the triflate and applied in palladium-catalyzed processes including Buchwald-Hartwig amination, Suzuki-Miyaura cross-coupling and sulfonylation reactions (30-32, Scheme 1c). Through this strategy, OTIPS OSF reagent 2 was readily converted to diverse oxetane analogues of important biologically active compounds with variation of the arene (Scheme 1d). Reaction of OTIPS OSF 2 with a primary amine followed by deoxygenative chlorination gave aryl chloride 34, an oxetane analogue to moclobemide, a marketed antidepressant. Reaction with a secondary amine and subsequent deoxygenation gave an oxetane analogue of donepezil (36), an Alzheimer's medication. Similarly, reaction with 2,3-dichloroaniline and phenol alkylation gave an oxetane analogue of rice herbicide etobenzanid (38). These sequences demonstrate the particular value of the OTIPS OSF 2 reagent for the divergent preparation of oxetane derivatives.