139214-37-2

Upstream product

• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 39758-39-9 diethyl [1-(4-fluorophenyl)vinyl]phosphate 
• 58518-77-7 ((1-(4-fluorophenyl)vinyl)oxy)trimethylsilane 
• 18243-38-4 (trimethylsilyl)methylmagnesium bromide 
• 139214-50-9 2-(4-fluorophenyl)-2-methyl-1,3-dithiane 

Relevant academic research and scientific papers

A Stereoselective Reductive Hosomi-Sakurai Reaction

A novel reductive variant of the classical Hosomi-Sakurai reaction is reported. This transformation hinges on a redox-neutral, stereoselective internal reduction event under mild conditions. This operationally simple reaction relies on readily available starting materials and leads to useful products in diastereoselectivities of up to 7:1. The versatility of this new method is demonstrated through the stereoselective one-step synthesis of an AChE inhibitor.

Silver-promoted cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides by palladium catalysis

A ligand-free Pd-catalyzed cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides enabled by silver salts was developed. This reaction delivered allylic arenes chemoselectively and regioselectively. The study suggested that the reaction might proceed through oxidative addition of ArI to Pd(0) followed by halide abstraction to give an electrophilic complex ArPdX, which further reacted with allyl(trimethyl)silanes via electrophilic addition/desilylation/reductive elimination to afford the allyl-aryl coupling products.

Trifluoromethylation of allylsilanes under copper catalysis

Branched allylic CF3 products are accessible by copper-catalyzed trifluoromethylation of allylsilanes with the Togni reagent I. The silyl group is critical to control the outcome of this reaction because in its absence, a product of addition be

Optimisation of the allylsilane approach to C-10 deoxo carba analogues of dihydroartemisinin: Synthesis and in vitro antimalarial activity of new, metabolically stable C-10 analogues

An optimised protocol has been developed for the coupling of dihydroartemisinin benzoate with a range of aromatic allylsilanes to provide a number of new C-10 deoxo derivatives (11a-11g) in yields ranging from 70 to 94%. These compounds were up to ten times more potent than artemisinin in in vitro tests against the chloroquine resistant K1 strain of Plasmodium falciparum. Ferrous mediated degradation of these analogues produces as the main product, a dicarbonyl formate 12, which is not seen when the same reaction is carried out with artemisinin or artemether. This finding may indicate that analogues in this class have a subtly different "antimalarial" mechanism of action.

The Effect of the Ring Size of the Dithiolato Leaving Group on the Orientation of β-Elimination in the Nickel-catalysed Alkenation of Cyclic Dithioacetals with Me3SiCH2MgCl

The product distribution (allyl- vs. vinyl-silanes) of the reactions of dithioacetals derived from alkyl aryl ketones with Me3SiCH2MgCl surprisingly depends on ring size of the cyclic dithioacetals, the five-membered ring substrates affording allylsilane as the major product while the six-membered analogues yield vinylsilanes predominantly.These results indicate that the leaving group, dithiolato moiety, may remain coordinated to the metal centre during the course of the catalytic process.