158953-96-9

Upstream product

• 811-98-3 d⁽⁴⁾-methanol 
• 123-54-6 acetylacetone 

Downstream Products

• 56999-62-3 ethyl 2-(1-methyl-1H-indol-3-yl)acetate 
• 1286254-54-3 1-phenyl-[4,4'-²H₂]-1,3-butadiene 
• 1646145-01-8 C₁₃H₁₄⁽²⁾HNO₂ 
• 603-76-9 1-methylindole 
• 1598431-21-0 (1S,2R)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 2-(1-methyl-1H-indol-3-yl)-5-oxocyclopentanecarboxylate 
• 1598431-76-5 (1R,2S)-(R)-1-(3,5-bis(trifluoromethyl)phenyl)ethyl 2-(1-methyl-1H-indol-3-yl)-5-oxocyclopentanecarboxylate 
• 1598431-73-2 (1R,2S)-(R)-1-(2,4,6-triisopropylphenyl)ethyl 2-(1-methyl-1H-indol-3-yl)-5-oxocyclopentanecarboxylate 
• 1598431-69-6 (1R,2S)-(S)-1-phenylethyl 2-(1-methyl-1H-indol-3-yl)-5-oxocyclopentanecarboxylate 
• 1062136-70-2 methyl 2-(1-methyl-1H-indol-3-yl)-2-phenylacetate 
• 1351620-41-1 C₁₈H₁₆⁽²⁾HNO₂ 
• 1287221-35-5 C₂₆H₂₄⁽²⁾HN 

Relevant academic research and scientific papers

Acid-catalyzed acylation reaction via C-C bond cleavage: A facile and mechanistically defined approach to synthesize 3-acylindoles

A facile acid-catalyzed acylation of indoles with 1,3-dione as an eco-friendly acylating agent was developed. This protocol combines C-C bond cleavage and heterocyclic C-H bond functionalization to form new C-C bonds. Based on the detailed mechanistic studies, a credible mechanistic pathway was proposed. This journal is

Metal-Free sp2-C-H Borylation as a Common Reactivity Pattern of Frustrated 2-Aminophenylboranes

C-H borylation is a powerful and atom-efficient method for converting affordable and abundant chemicals into versatile organic reagents used in the production of fine chemicals and functional materials. Herein we report a facile C-H borylation of aromatic and olefinic C-H bonds with 2-aminophenylboranes. Computational and experimental studies reveal that the metal-free C-H insertion proceeds via a frustrated Lewis pair mechanism involving heterolytic splitting of the C-H bond by cooperative action of the amine and boryl groups. The adapted geometry of the reactive B and N centers results in an unprecedentently low kinetic barrier for both insertion into the sp2-C-H bond and intramolecular protonation of the sp2-C-B bond in 2-ammoniophenyl(aryl)- or -(alkenyl)borates. This common reactivity pattern serves as a platform for various catalytic reactions such as C-H borylation and hydrogenation of alkynes. In particular, we demonstrate that simple 2-aminopyridinium salts efficiently catalyze the C-H borylation of hetarenes with catecholborane. This reaction is presumably mediated by a borenium species isoelectronic to 2-aminophenylboranes.