103872-45-3

Upstream product

• 16199-06-7 potassium pyrrolide 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 20671-52-7 lithium pyrrolide 
• 109-97-7 pyrrole 
• 2357-76-8 tert-butyldimethylfluorosilane 

Downstream Products

• 89902-45-4 tert-butyldimethylsilyl trifluoromethanesulfonate 
• 13169-74-9 2-phenyl-1-(1H-pyrrol-2-yl)ethanone 
• 103872-47-5 [1-(tert-Butyl-dimethyl-silanyl)-1H-pyrrol-3-yl]-phenyl-methanone 
• 103872-48-6 1-[1-(tert-Butyl-dimethyl-silanyl)-1H-pyrrol-3-yl]-2-phenyl-ethanone 
• 96999-24-5 2-phenyl-1-(1H-pyrrol-3-yl)ethanone 
• 7697-46-3 phenyl(1H-pyrrol-2-yl)methanone 
• 109-97-7 pyrrole 

Relevant academic research and scientific papers

Synthesis of 3-hetarylpyrroles by Suzuki–Miyaura cross-coupling

1-[tert-Butyl(diphenyl)silyl]pyrrol-3-ylboronic acid was obtained from pyrrole in three steps. Its Suzuki–Miyaura cross-coupling with functionalized pyridinyl and pyrimidinyl bromides afforded new promising 3-hetaryl-1H-pyrroles.

Indole- and Pyrrole-BX: Bench-Stable Hypervalent Iodine Reagents for Heterocycle Umpolung

The one-step synthesis of the bench-stable hypervalent iodine reagents IndoleBX and PyrroleBX using mild Lewis acid catalyzed conditions is reported. The new reagents are stable up to 150 °C and were applied in the C?H arylation of unactivated arenes using either rhodium or ruthenium catalysts. A broad range of heterocyclic systems of high interest for synthetic and medicinal chemistry was accessed in high yields. The developed C?H functionalization could not be achieved using reported reagents or methods, highlighting the unique reactivity of Indole- and Pyrrole-BX.

Indolyl- and Pyrrolylsilanes - Syntheses and Crystal Structures

Lithium indolide and lithium pyrrolide react with fluoro- and chlorosilanes with formation of mono- and bis(indol-1-yl)- and -(pyrrol-1-yl)silanes, tris- and tetrakis(pyrrol-1-yl)silanes as well as of silanes substituted with different heteroaromatic syst

Studies in the Protection of Pyrrole and Indole Derivatives

Treatment of pyrrole (1a), 2,5-dimethylpyrrole (1b), indole (3a), 2-methylindole (3b), 3-methylindole (3c), 2,3-dimethylindole (3d), 1,2,3,4-tetrahydro-9H-carbazole (5a), 5,6,7,8,9,10-hexahydrocycloheptindole (5b), and 6,7,8,9,10,11-hexahydro-5H-cyclo-octindole (5c) with sodium hydride in tetrahydrofuran, followed by phenyl t-butyl carbonate (8) gives the corresponding N-t-butoxycarbonyl (t-BOC) derivatives in satisfactory yields.By using chlorodimethyl-t-butylsilane instead of (8), N-dimethyl-t-butylsilyl derivatives are obtained, also in satisfactory yields.The use of the 2-(trimethylsilyl)ethoxycarbonyl (TEOC) group for the N-protection of the indole system, and the pivaloyloxymethyl (POM) group for the N-protection of the pyrrole and indole systems is also described.

FRIEDEL-CRAFTS ACYLATION OF 1-TERT-BUTYLDIMETHYLSILYLPYRROLE, A VERY SHORT AND SIMPLE ROUTE TO 3-SUBSTITUTED PYRROLES.

1-tert-Butyldimethylsilylpyrrole undergoes Friedel-Crafts acylation almost exclusively at β-position giving after sodium fluoride supported hydrolysis the 3-pyrroloketones.