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Exclusive selectivity in the one-pot formation of C–C and C–Se bonds involving Ni-catalyzed alkynes hydroselenation: Optimization of the synthetic procedure and a mechanistic studyстатья
Статья опубликована в высокорейтинговом журнале
Статья опубликована в журнале из списка Web of Science и/или Scopus- Авторы: Orlov N.V., Chistyakov I.V., Khemchyan L.L., Ananikov V.P., Beletskaya I.P., Starikova Z.A.
- Журнал: Journal of Organic Chemistry
- Год издания: 2014
- Издательство: American Chemical Society
- Местоположение издательства: United States
- DOI: 10.1021/jo501953f
- Аннотация: Article ASAP A unique Ni-catalyzed transformation is reported for the one-pot highly selective synthesis of previously unknown monoseleno-substituted 1,3-dienes starting from easily available terminal alkynes and benzeneselenol. The combination of a readily available catalyst precursor, Ni(acac)2, and an appropriately tuned phosphine ligand, PPh2Cy, resulted in the exclusive assembly of the s-gauche diene skeleton via the selective formation of C–C and C–Se bonds. The unusual diene products were stable under regular experimental conditions, and the products maintained the s-gauche geometry both in the solid state and in solution, as confirmed by X-ray analysis and NMR spectroscopy. Thorough mechanistic studies using ESI-MS revealed the key Ni-containing species involved in the reaction.
- Добавил в систему: Анаников Валентин Павлович