Traditionally, 1,2-amino alcohols are prepared by a nucleophilic attack of an amine to an epoxide. However, the limited availability and difficulties in the synthesis of epoxides in a late-stage application calls for an alternative method. 42 The development of a complementary method using commercially available starting materials for 1,2-amino alcohol synthesis is highly desired. Accordingly, secondary amines were used as nucleophilic C-H carbanion precursors with various carbonyl compounds as electrophiles to give the corresponding 1,2-amino alcohol in moderate to good yields (Fig. ). The reaction conditions were only slightly changed, with DABCO proving to be superior to K2CO3 as a base (Table -S8). With acetone as an electrophile, substrates bearing electron-donating and -withdrawing substituents on the aromatic ring gave the respective amino alcohol in good yields up to 80% (Fig. , 31-38). The low yield in case of the strong electron-withdrawing cyano group (37) could be ascribed to an incomplete conversion, where most of the remaining starting material was recovered after the completed reaction time. Aromatic and aliphatic amides instead of esters could be used as carbanion stabilizing groups as well. Similarly, a conjugated electron-withdrawing moiety (41) was viable, too. Unfortunately, products 40 and 41 were only obtained in low yields of 16 and 19%, respectively. The diminished yield in these cases may be attributed to the decomposition of the products at room temperature. In the scope of amines shown in Fig. , acetone was used as a co-solvent in order to achieve the optimal yield. However, the use of comparatively less equivalents (10 equivalents) of acetone lowers to yield only slightly. As an example, a good yield of 70% could still be obtained in case of compound 31. Notably, deuterated acetone could be used as an electrophile to give the corresponding amino alcohol 42 in an isolated yield of 80%, too. Besides acetone, different aliphatic aldehydes and ketones can be employed as electrophiles to give the corresponding product (Fig. ). Aromatic carbonyl compounds were not included in this study, as they may be directly reduced by the radical anion of the photocatalyst. With a reduction potential of -1.92 V vs. SCE, 33 the reduced 3DPA2FBN species is in reach of e.g. benzaldehyde (E red 1/2 = -1.93 V vs. SCE) and benzophenone (E red 1/2 = -1.83 V vs. SCE). A potential product formation would hence likely involve a radical-radical cross-coupling mechanism rather than a carbanion formation. 57 Noteworthy, 2-3 equivalents of carbonyl compound are sufficient to give the desired product in good yields (Fig. ). Cyclic , as well as linear (47) aldehydes, gave the desired products in a yield of 70-80%. Similarly, the use of cyclic ketones led to good yields of 62-72%. Interestingly, Nabumetone as an example for a linear ketone is a viable electrophile, yielding 53 in 47%. In order to demonstrate the applicability of this method further, compounds 1, 31, and 42 were prepared in a bulk-scale (1-2 g scale). A yield of 60-70% was obtained (Scheme S4-S6), which is comparable to the small-scale synthesis. Moreover, the cleavage of the PMP protecting group was tested for the deuterated model compound 1, applying a previously reported cerium ammonium nitrate method. 58 Gratifyingly, the corresponding secondary amine was obtained, retaining the same deuterium incorporation (Scheme S7). In this context, alpha deuterated/tritiated secondary or primary amines can be synthesized by this pathway.