Abstract
This study describes, for the first time, the in situ generation of indium organometallic reagents in environmentally friendly deep eutectic solvents (DESs). The allylation process of different carbonyl compounds is achieved mediated by indium metal and using cheap allyl chloride derivatives. The unique DES properties allow to perform the reaction at room temperature and under air, obtaining yields ranging from 45% to 99%. It is possible to recycle the reaction medium for at least four consecutive cycles without much decrease of the observed results. Also, a linear correlation between the yield of the reaction and the density of the DESs is observed.
Highlights
The allylation of carbonyl compounds via allylmetal reagents is one of the most valuable transformations in Organic Synthesis because it creates a new C C bond and a stereocenter.[1]
The allylation process of carbonyl compounds has been described with different metals (Ga, Zn, Sn, etc.), with indium reagents offering several advantages, because they are minimally toxic, compatible with a great variety of functional groups, and stable to air and moisture (Scheme 1).[3]
This Barbier-type allylation process has been previously performed in classical organic solvents,[4a,b] water,[4c,d] ionic liquids (ILs),[4e–k] and under solvent-free conditions.[4l–n]
Summary
The allylation of carbonyl compounds via allylmetal reagents is one of the most valuable transformations in Organic Synthesis because it creates a new C C bond and a stereocenter.[1]. When 28 mol% of ammonium acetate was added, compound 3a was obtained in both mixtures with excellent yields (Entries 11 and 12, footnote c).
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
