Ian MacLean , Montaña J. García , Silvia Cabrera , Leyre Marzo , José Alemán
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引用次数: 0
Abstract
In this work, we present a sustainable and environmentally benign electrochemical method for the synthesis of β-keto spirolactones. The reaction is carried out using green solvents such as acetone and water, and simple electrons as oxidants, instead of the stoichiometric oxidants used in classical approaches. The robustness of the method allows the functionalization of cyclic β-keto esters and a β-keto amide, the latter affording α-spiroiminolactone. The method also gives good results with double bonds bearing substituents of different electronic natures. Furthermore, this methodology can be easily scalable through a continuous flow electrochemical approach that improves the productivity of the reaction. Mechanistic investigations support the radicalic nature of the transformation, and the generation of a carbocation intermediate that is further trapped with the water employed as co-solvent in the reaction.
期刊介绍:
Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.