1369371-65-2

Upstream product

• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 17151-09-6 1,2-bis(trimethylsilyl)benzene 
• 1369371-68-5 4-pinacolatoboryl-1,2-bis(trimethylsilyl)benzene 
• 1369371-66-3 3,5-dibromo-1,2-bis(trimethylsilyl)benzene 
• 19978-33-7 5-bromo-2H-pyran-2-one 

Downstream Products

• 101300-64-5 1,2-bis(trimethylsilyl)-4-methylbenzene 
• 1449112-70-2 C₃₁H₃₁B₂Br 
• 1449112-71-3 C₃₁H₃₁B₂Br 
• 1449112-68-8 C₃₀H₂₈B₂Br₂ 
• 1449112-69-9 C₃₀H₂₈B₂Br₂ 
• 1449112-72-4 C₃₂H₃₃B₂Br 
• 1449112-77-9 4-bromo-1-(dibromoboryl)-2-(trimethylsilyl)benzene 
• 1449112-92-8 C₆₆H₅₆B₂N₂ 
• 1449112-93-9 C₆₆H₅₆B₂N₂ 
• 1449112-86-0 C₃₈H₃₄B₂S₂ 
• 1449112-87-1 C₃₈H₃₄B₂S₂ 
• 1449112-88-2 C₃₆H₃₆B₂S 

Relevant academic research and scientific papers

Synthesis of bromo-, boryl-, and stannyl-functionalized 1,2-bis(trimethylsilyl)benzenes via Diels-Alder or C-H activation reactions

1,2-Bis(trimethylsilyl)benzenes are key starting materials for the synthesis of benzyne precursors, Lewis acid catalysts, and certain luminophores. We have developed efficient, high-yield routes to functionalized 4-R-1,2-bis(trimethylsilyl)benzenes, starting from either 1,2- bis(trimethylsilyl)acetylene/5-bromopyran-2-one (2) or 1,2-bis(trimethylsilyl) benzene (1)/bis(pinacolato)diborane. In the first reaction, 5 (R = Br) is obtained through a cobalt-catalyzed Diels-Alder cycloaddition. The second reaction proceeds via iridium-mediated C-H activation and provides 8 (R = Bpin). Besides its use as a Suzuki reagent, compound 8 can be converted into 5 with CuBr2 in i-PrOH/MeOH/H2O. Lithium-bromine exchange on 5, followed by the addition of Me3SnCl, gives 10 (R = SnMe3), which we have applied for Stille coupling reactions. A Pd-catalyzed C-C coupling reaction between 5 and 8 leads to the corresponding tetrasilylbiphenyl derivative. The bromo derivative 5 cleanly undergoes Suzuki reactions with electron-rich as well as electron-poor phenylboronic acids.