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![]() GÎRBU, Vladilena, UNGUR, Nikon, KULCIŢKI, Veaceslav, RENAUD, Philippe. Radical perfluoroalkylation of ENT-kaurenoate derivatives. In: Achievements and perspectives of modern chemistry, 9-11 octombrie 2019, Chişinău. Chisinau, Republic of Moldova: Tipografia Academiei de Ştiinţe a Moldovei, 2019, p. 219. ISBN 978-9975-62-428-2. |
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Achievements and perspectives of modern chemistry 2019 | ||||||
Conferința "International Conference "Achievements and perspectives of modern chemistry"" Chişinău, Moldova, 9-11 octombrie 2019 | ||||||
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Pag. 219-219 | ||||||
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Rezumat | ||||||
Atom transfer radical addition (ATRA) to alkenes provides a useful tool to create C-C and C-X bonds in a single synthetic step [1-3]. It offers some attractive routes to synthesize the pharmaceutically important molecules. Reductive ATRA represents one of the mildest procedures for a formal alkene carbohydrogenation. We report the application of a mild and convenient reductive ATRA procedure [5], in order to generate a series of methyl ent-kaurenoate 1 fluorinated derivatives 2-6 (Figure). Carbohydrogenation of methyl ent-kaurenoate 1 was performed with several iodo-radical precursors under very mild conditions, in the presence of triethylborane and oxygen (open air) as radical initiators and 4-methoxycatechol as a reducing agent.formulaFigure. Carbohydrogenation of ent-kaurenoate ester. (*tert-butylcatechol (TBC) was used) Hydroalkylation of ent-kaurene derivatives with perfluoroalkyl iodides as radical precursor afforded the fluorinated compounds 2-6 in very good yields (75-87%). These compounds will be tested for biological activity in the following studies towards implementation in medicine or radiology. |
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