Lateral lithiation in deep eutectic solvents: regioselective functionalization of substituted toluene derivatives

Abstract

Ultrafast heteroatom-directed lateral lithiation of substituted toluene derivatives using choline chloride-based eutectic mixtures as bio-inspired sustainable reaction media.

Solvent-controlled O2 diffusion enables air-tolerant solar hydrogen generation

“…DESs are an alternative class of low-cost, highly tuneable ionic liquids 23 that can be prepared from readily available precursors and possess lower toxicities than conventional ionic liquids. 24 DESs have been employed for airtolerant organic reactions involving highly reactive organolithium compounds 25,26 and it has recently been shown they can stabilise O 2 -sensitive radicals in air. 27 Using a carbon nitride photocatalyst, we now show that DESs create a nearanaerobic environment in which up to 97% of the photocatalytic H 2 evolution activity is retained under air (Fig.…”

Radical-mediated thiol–ene ‘click’ reactions in deep eutectic solvents for bioconjugation

“…21 Furthermore, the exploitation of DESs as solvents and/or catalysts for organic reactions has been a recent and intense area of study. Several archetypical reactions [22][23][24][25] including Grignard and organolithium additions [26][27][28] as well as the preparation of pharmaceutical active ingredients, 29 have been optimised in these protic media.…”

Promising Technological and Industrial Applications of Deep Eutectic Systems

“…The authors extended their methodology and investigated the lateral lithiation (LL) in DES on several o-tolyl-tertiary amides, sulfonamides and oxazolines, providing the DLL products functionalized with several electrophiles, over very short reaction times (Scheme 7) [151]. The authors extended their methodology and investigated the lateral lithiation (LL) in DES on several o-tolyl-tertiary amides, sulfonamides and oxazolines, providing the DLL products functionalized with several electrophiles, over very short reaction times (Scheme 7) [151].…”

“…The authors extended their methodology and investigated the lateral lithiation (LL) in DES on several o -tolyl-tertiary amides, sulfonamides and oxazolines, providing the DLL products functionalized with several electrophiles, over very short reaction times ( Scheme 7 ) [ 151 ].…”