1006715-22-5

Upstream product

• 402-26-6 3-(trifluoromethyl)phenylmagnesium bromide 
• 768-33-2 phenyldimethylsilyl chloride 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 3839-31-4 dimethyl(phenyl)silyl lithium 
• 544-97-8 dimethyl zinc(II) 
• 141738-80-9 2-chloro-1-iodo-4-(trifluoromethyl)benzene 

Relevant academic research and scientific papers

Suzuki-type cross coupling between aryl halides and silylboranes for the syntheses of aryl silanes

Herein we report Pd catalyzed Suzuki type cross coupling between aryl halides and silylboranes for the syntheses of aryl silanes. This reaction shows a general substrate scope, excellent compatibility with electrophilic functionalities and good yields.

Zinc-catalyzed nucleophilic substitution reaction of chlorosilanes with organomagnesium reagents

Zinc-catalyzed nucleophilic substitution reactions of chlo-rosilanes with organomagnesium reagents afford various tetraorganosilanes under mild reaction conditions. The reactions can be performed on large scale and allow efficient preparation of functionalized tetraorganosilanes.

Copper-catalyzed arylation of chlorosilanes with grignard reagents

Nucleophilic substitution reactions of chlorosilanes with aryl Grignard reagents take place efficiently in the presence of copper(I) iodide to afford tetraorganosilanes.

Silver-catalyzed transmetalation between chlorosilanes and aryl and alkenyl Grignard reagents for the synthesis of tetraorganosilanes

(Chemical Equation Presented) The silver savior: Nucleophilic substitution reactions of chlorosilanes with aryl Grignard reagents have been developed which take place under silver catalysis to afford tetraorganosilanes (see scheme). This transformation is likely to be promoted by diarylargentate reagents that are generated in situ.

Generation and suppression of 3-/4-functionalized benzynes using zinc ate base (TMP-Zn-ate): New approaches to multisubstituted benzenes

We present full details of our new methods for preparing functionalized benzynes with lithium di-alkyl(2,2,6,6-tetramethylpiperidino)zincate (R 2Zn(TMP)Li) through deprotonative zincation as a key reaction. In this system, by choosing appropriate ligands for the zincate, either regioselective zincation of functionalized haloaromatics or the generation of substituted benzynes can be controlled in good yields with excellent chemoselectivity, using the same substrate. Zincation with tBu 2Zn(TMP)Li followed by electrophilic trapping or zincation with Me2Zn(TMP)Li followed by nucleophilic or diene trapping is shown to be a powerful tool for the chemoselective preparation of 1,2,3-/1,2,4- trisubstituted benzene derivatives. These methods offer far greater generality than previous methods for the synthesis of multifunctionalized benzenes. Computational/theoretical studies of the reaction mechanism of this unique benzyne formation indicated that preferential coordination of the dialkylzinc moiety of zincate to halogen is the reason for the reduced activation energy of the elimination, that is, for the formation of the benzyne. The role of the ligands on Zn in accelerating/decelerating the elimination is also discussed.