1855-13-6Relevant articles and documents
Barbier-type reactions of aryl halides with ketones mediated by Samarium diiodide
Kunishima,Hioki,Kono,Sakuma,Tani
, p. 2190 - 2192 (1994)
Barbier-type reaction of aryl halides with ketones took place on treatment with samarium diiodide in benzene containing 10% hexamethylphosphoric triamide (HMPA). The reaction involves an aryl samarium as an intermediate.
Expeditious and practical synthesis of tertiary alcohols from esters enabled by highly polarized organometallic compounds under aerobic conditions in Deep Eutectic Solvents or bulk water
Quivelli, Andrea F.,D'Addato, Giovanna,Vitale, Paola,García-álvarez, Joaquín,Perna, Filippo M.,Capriati, Vito
, (2021/01/18)
An efficient protocol was developed for the synthesis of tertiary alcohols via nucleophilic addition of organometallic compounds of s-block elements (Grignard and organolithium reagents) to esters performed in the biodegradable choline chloride/urea eutectic mixture or in water. This approach displays a broad substrate scope, with the addition reaction proceeding quickly (20 s reaction time) and cleanly, at ambient temperature and under air, straightforwardly furnishing the expected tertiary alcohols in yields of up to 98%. The practicability of the method is exemplified by the sustainable synthesis of some representative S-trityl-L-cysteine derivatives, which are a potent class of Eg5 inhibitors, also via telescoped one-pot processes.
Directed: Ortho-metalation-nucleophilic acyl substitution strategies in deep eutectic solvents: The organolithium base dictates the chemoselectivity
Ghinato, Simone,Dilauro, Giuseppe,Perna, Filippo Maria,Capriati, Vito,Blangetti, Marco,Prandi, Cristina
, p. 7741 - 7744 (2019/07/12)
Directed ortho metalation (DoM) or nucleophilic acyl substitution (SNAc) can be efficiently programmed on the same aromatic carboxylic acid amide, in a choline chloride-based eutectic mixture, by simply switching the nature of the organolithium reagent. Telescoped, one-pot ortho-lithiation/Suzuki-Miyaura cross-couplings have also been demonstrated for the first time in Deep Eutectic Solvents.
