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The ring-opening of cyclic ethers (epoxide, oxetane, THF, and THP) by carboxylic acids was achieved by using N-iodosuccinimide (NIS) or N-bromosuccinimide (NBS) and triphenylphosphine under the irradiation of blue light. The corresponding omega-haloalkyl carboxylates were obtained under mild reaction conditions. The reaction is believed to work through a halogen bond complex between NIS (or NBS) and triphenylphosphine, which, upon irradiation with blue light, produces the key phosphine radical cation intermediate that initiates the ring-opening reactions.
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A direct one-pot alkylation-aminoxidation of styrene derivatives was achieved by using in-situ-generated alkyl and N-oxyl radicals. The corresponding O-alkylated hydroxylamine derivatives were obtained in moderate to good yields. The reaction features the generation of the alkyl radicals from phenyliodine(III) dicarboxylates via an organocatalytic process, the use of phenyliodine(III) dicarboxylates as the source of the alkyl radicals and the oxidant for the generation of the N-oxyl radicals, and the first generation of the β-enaminyl radicals via a HAT process and their use as the single-electron donors.more » « less
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The α-acyloxylcarbonyl motif can be found in many important pharmaceuticals and biologically active natural products and their derivatives. In this manuscript, the direct synthesis of α-acyloxylketones from ketones and readily available carboxylic acids was realized using a photo-assisted halogen bond-mediated organocatalytic α-acyloxylation reaction. The desired α-acyloxylation products were obtained in good to high yields.more » « less
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A highly enantio- and diastereoselective method for the synthesis of functionalized chroman-2-ones and chromanes was achieved by using an organocatalytic domino Michael/hemiacetalization reaction of aliphatic aldehydes and ( E )-2-(2-nitrovinyl)phenols followed by a PCC oxidation and dehydroxylation, respectively. Using the modularly designed organocatalysts (MDOs) self-assembled from cinchona alkaloid derivatives and amino acids in the reaction media, the title products were obtained in good to high yields (up to 97%) and excellent diastereoselectivities (up to 99 : 1 dr) and enantioselectivities (up to 99% ee).more » « less
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The domino Michael/Michael reaction between ( E )-7-aryl-7-oxohept-5-enals and trans -cinnamaldehydes was investigated by using modularly designed organocatalysts (MDOs). It was found that both the enamine and iminium catalytic modes of the MDOs are switchable and can be individually switched on and off by using appropriate combinations of the precatalyst modules and the reaction conditions. When both the enamine and iminium catalysis modes of the MDOs are switched on, the desired domino reaction products can be obtained in good yields and stereoselectivities under optimized conditions.more » « less
