1283154-24-4

Upstream product

• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 14070-53-2 N-benzyl-N-chloro-4-methylbenzenesulfonamide 
• 707-07-3 orthobenzoic acid trimethyl ester 
• 768-33-2 phenyldimethylsilyl chloride 
• 70-55-3 toluene-4-sulfonamide 
• 3839-31-4 dimethyl(phenyl)silyl lithium 
• 22158-84-5 N-(p-Toluolsulfonyl)-benzimidsaeure-methylester 
• 931-50-0 cyclohexylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 51608-60-7 phenyl N-tosyl imine 

Relevant academic research and scientific papers

Copper-Catalyzed Silylation of C(sp3)-H Bonds Adjacent to Amide Nitrogen Atoms

A copper-catalyzed C-Si bond formation between N-halogenated amides and Si-B reagents is described. This oxidative coupling enables the silylation of C(sp3)-H bonds α to an amide nitrogen atom. The utility of the new method is demonstrated for

Efficient synthesis of α-tertiary α-silylamines from aryl sulfonylimidates via one-pot, sequential C-Si/C-C bond formations

An efficient and flexible route for the synthesis of α-tertiary (α,α-dibranched) α-silylamines via sequential reactions of sulfonylimidates using readily available phenyldimethylsilyllithium and Grignard reagents is described. The procedure allows successive formation of C-Si/C-C bonds in a single flask.

Activation of the Si-B Linkage: Copper-Catalyzed addition of nucleophilic silicon to imines

Activation of the Si-B bond through copper-catalyzed transmetalation quickly developed into a practical method to generate Cu-Si reagents These silicon nucleophiles cleanly add to aldehyde-derived imine electrophiles to form R-silylated amines in protic media, and no carbon-tonitrogen Brook-type rearrangement of the intermediate anion is observed. Aside from electron-withdrawing groups at the imine nitrogen atom, for example, SO2Tol and P(O)Ph2, previously delicate nitrogen substituents such as phenyl or benzhydryl are tolerated. The same protocol also allows the unprecedented addition to representative ketone-derived imines.