1313182-27-2

Upstream product

• 154345-34-3 2-bromo-4-methyl-6-(trimethylsilyl)phenol 
• 1313182-64-7 trimethylsilyl 2-bromo-4-methyl-6-(trimethylsilyl)phenyl ether 
• 18033-63-1 4-methyl-2,6-bis(trimethylsilyl)phenol 
• 109-73-9 N-butylamine 
• 97391-19-0 4-methyl-2,6-bis(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 154345-10-5 2-bromo-4-methyl-6-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 1245635-42-0 4-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trimethylsilyl)phenyl trifluoromethanesulfonate 

Relevant academic research and scientific papers

Ortho-Selective nucleophilic addition of amines to 3-borylbenzynes: Synthesis of multisubstituted anilines by the triple role of the boryl group

Nucleophilic addition of amines to 3-[(dan)boryl]benzynes (dan = 1,8-diaminonaphthalene) generated by a fluoride ion proceeded with high ortho-selectivity to give 2-borylaniline derivatives, under conditions that are tolerant to various functional groups. The (dan)boryl group of the adduct was hydrolyzed into a boronic acid under acidic conditions, which could further serve for various C-C, C-O, C-N, and C-H bond-formation reactions. The overall process provides a promising entry for preparing multisubstituted aniline derivatives.

Ortho-selective nucleophilic addition of primary amines to silylbenzynes: Synthesis of 2-silylanilines

Cause and effect: The first ortho-selective nucleophilic addition reaction of amines to 3-substituted benzynes has been achieved. Despite a large trimethylsilyl substituent, primary amines attack the C2 position of 3-silylbenzynes to produce 2-silylanilines (see scheme). This outcome is likely to result from the inductive electron-donating effect of the silyl group, which overrides its steric repulsion with the approaching amines. Copyright