Expanding Blaise-Type Reactions towards Indium-Mediated Transformations of α-Bromo-β-keto Esters with Nitriles

Autor:	Luomo Li, Emre Babaoglu, Klaus Harms, Gerhard Hilt
Rok vydání:	2017
Předmět:	Reaction conditions 010405 organic chemistry Chemistry Organic Chemistry chemistry.chemical_element 010402 general chemistry Indium metal 01 natural sciences 0104 chemical sciences Indium Trichloride Blaise reaction Organic chemistry Lewis acids and bases Physical and Theoretical Chemistry Indium
Zdroj:	European Journal of Organic Chemistry. 2017:4543-4547
ISSN:	1434-193X
DOI:	10.1002/ejoc.201700868
Popis:	The aim of this work is the identification of mild reaction conditions for the Blaise-type transformation of brominated β-keto esters with nitriles to generate enamino-substituted keto esters. The best results were obtained when a combination of indium metal (0.7 equiv.) with indium trichloride (1.6 equiv.) were applied at 60 °C for 20 to 72 hours, and these conditions could be applied to a broad range of nitriles and a significant number of different β-keto esters. The transformation of aliphatic nitriles proved to be difficult and gave only moderate yields. However, aromatic nitriles gave good yields in many cases. The applicability range of β-keto esters is acceptable while some electron-deficient aryl-substituents on the keto ester were challenging substrates. Nevertheless, we were able to expand the scope of the Blaise-type reaction towards brominated β-keto esters significantly.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::358748a8d1bca8285af44277ba23322b https://doi.org/10.1002/ejoc.201700868 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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