History and catalyst development[ edit ] Copper monometallic systems[ edit ] The first reported decarboxylative cross coupling reaction was an Ullmann reactionin by Nilsson et al. Thermal decarboxylation of copper benzoates, in the presence of an aryl halidewas found to produce both symmetric and unsymmetric biaryls through aryl-Cu intermediates. The oxidative addition step was determined to be the rate-limiting step in the copper-only catalyst cycle a contrast with Pd-catalyzed decarboxylative cross-coupling.
Synthesis of alkyl azides Recent Literature A practical, rapid, and efficient microwave MW promoted nucleophilic substitution of alkyl halides or tosylates with alkali azides, thiocyanates or sulfinates in aqueous media tolerates various reactive functional groups.
Azide transfer of 2-azido-1,3-dimethylimidazolinium hexafluorophosphate ADMP to alcohols proceeds to give the corresponding azides under mild reaction conditions. The organic azides were easily isolated because the byproducts are highly soluble in water. Okauchi, Synlett,23, With AgNO3 as the catalyst and K2S2O8 as the oxidant, an efficient and general method for the decarboxylative azidation of aliphatic carboxylic acids with tosyl azide or pyridinesulfonyl azide in aqueous MeCN solution afforded the corresponding alkyl azides under mild conditions.
A broad substrate scope and wide functional group compatibility were observed. A radical mechanism is proposed. In a catalytic decarboxylative nitrogenation, a series of tertiary, secondary, and primary organoazides were prepared from easily available aliphatic carboxylic acids by using K2S2O8 as the oxidant and PhSO2N3 as the nitrogen source via an alkyl radical process.
Carreira, Synthesis, The combination of sodium periodate, potassium iodide, and sodium azide is an efficient, simple, and inexpensive reagent system for azidoiodination of alkenes. Sudalai, Synthesis,Yan, M.; Kawamata, Y; Baran, P.
S. Synthetic Organic Electrochemical Methods Since On the Verge of a Renaissance. Chem.
Rev. , , Decarboxylative cycloaromatization of enediyne model compounds—mechanism of the radical and ionic pathway. A series of decarboxylative cycloaromatization reactions under various conditions were carried out and the results are summarized in Table 2.
substantiates the radical mechanism of . Synthesis of (MeO) 2 Bn 2 C Regiochemistry of 2-fold Additions to C 70 with Addends That Are Preferential for Ortho Addition and Capable of Para Addition.
Catalyst-Free and Redox-Neutral Innate Trifluoromethylation and Alkylation of Aromatics Enabled by Light Journal of the American Chemical Society. Categories: C-N Bond Formation > Synthesis of azides > Synthesis of alkyl azides.
Recent Literature. A practical, rapid, and efficient microwave (MW) promoted nucleophilic substitution of alkyl halides or tosylates with alkali azides, thiocyanates or sulfinates in aqueous media tolerates various reactive functional groups. 27 “Scope and Mechanism of Enantioselective Michael Additions of 1,3-Dicarbonyl Compounds to Nitroalkenes Catalyzed by Nickel(II)-Diamine Complexes.”.