26663-50-3

Upstream product

• 694-53-1 phenylsilane 
• 112398-75-1 5-chloro-1-methyl-1H-indole 
• 789-25-3 HSiPh₃ 
• 775-12-2 diphenylsilane 

Downstream Products

• 112398-75-1 5-chloro-1-methyl-1H-indole 
• 60434-13-1 5-chloro-1-methylindoline-2, 3-dione 

Relevant academic research and scientific papers

B(C6F5)3-Catalyzed (Convergent) Disproportionation Reaction of Indoles

A metal-free B(C6F5)3-catalyzed approach is developed for the disproportionation reaction of a series of indoles with various hydrosilanes, without any additives such as base and production of any small molecule such as dihydrogen. This boron catalyst system also exhibits excellent catalytic performance for practical application, such as catalyst loading as low as 0.01 mol % under solvent-free conditions, and a long-life catalytic performance highlighted by a constant catalytic activity being maintained and excellent yields being achieved for the desired products over 10 sequential additions of starting materials. On the basis of characterization of key intermediates through a series of in situ NMR reactions and detailed experimental data, we proposed a reaction mechanism which illustrated pathways for the formation of different products, including both major products and byproducts. Additional control experiments were conducted to support our proposed mechanism. Understanding the mechanism enables us to successfully suppress side reactions by choosing appropriate substrates and hydrosilanes. More importantly, the use of an elevated reaction temperature for continuous oxidation of the resulting indoline to indole makes the convergent disproportionation reaction an ideal atom-economical process. Near-quantitative conversions and up to 99% yields of C3-silylated indoles were achieved for various indoles with trisubstituted silanes, Ph3SiH (2b) or Ph2MeSiH (2d).

Catalytic system for efficiently catalyzing indole silanization and proton transfer hydrogenation

The invention discloses a catalytic system for efficiently catalyzing indole silanization and proton transfer hydrogenation, and belongs to the technical field of organic synthesis. According to the catalytic system, indole and silane serve as raw materials, tris(pentafluorophenyl) boron (B (C6F5)3) serves as a catalyst, reaction is performed for 10 minutes at the indoor temperature to simultaneously achieve 3-position selective indole silanization and proton transfer hydrogenation or reaction is performed for 10-1440 minutes at the temperature ranging from 100 DEG C to 140 DEG C to achieve 3-position efficient and specific catalytic indole silanization. The catalytic system has the advantages that the catalytic system is convenient to operate, mild in reaction condition, rapid in reaction, high in conversion rate, less in catalyst consumption and applicable to various solvent systems or body systems without any solvents, raw materials are easily acquired, precious metal is omitted, a catalytic intermediate is high in stability and the like.