763138-83-6

Basic information

• Product Name: 1,1'-bis-(toluene-4-sulfonyl)-1H,1'H-[3,3']biindolyl
• Synonyms: 1,1'-bis-(toluene-4-sulfonyl)-1H,1'H-[3,3']biindolyl
• CAS NO: 763138-83-6
• Molecular Weight: 540.664
• Mol File: 763138-83-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,1'-bis-(toluene-4-sulfonyl)-1H,1'H-[3,3']biindolyl(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-bis-(toluene-4-sulfonyl)-1H,1'H-[3,3']biindolyl(763138-83-6)
• EPA Substance Registry System: 1,1'-bis-(toluene-4-sulfonyl)-1H,1'H-[3,3']biindolyl(763138-83-6)

Safety Data

• Hazardous Substances Data: 763138-83-6(Hazardous Substances Data)

Upstream product

• 13472-61-2 5-iodo-2-methoxypyridine 
• 90481-77-9 3-bromo-1-(4-methylbenzenesulfonyl)-1H-indole 
• 23889-85-2 4-iodo-1-phenyl 1H-pyrazole 
• 73852-88-7 2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 135862-47-4 p-(1,3-Dioxolan-2-yl)iodobenzene 
• 23062-41-1 3-bromo-4-phenylthiophene 
• 455-13-0 4-Iodobenzotrifluoride 
• 170456-80-1 3-iodo-1-tosyl-1-indole 
• 1073354-51-4 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-p-toluenesulfonyl-1H-indole 
• 120-72-9 indole 
• 26340-47-6 3-Iodo-1H-indole 
• 2423-65-6 Pyrazin-N-Oxid(PyzNO) 
• 31271-90-6 1-(p-toluenesulfonyl)-1H-indole 
• 763138-80-3 1,1'-bis-(toluene-4-sulfonyl)-2,3-dihydro-1H,1'H-[3,3']biindolyl 

Downstream Products

• 13637-37-1 1H,1'H-[3,3']biindolyl 

Relevant articles and documents

Zirconium-redox-shuttled cross-electrophile coupling of aromatic and heteroaromatic halides

Transition metal-catalyzed cross-electrophile coupling (XEC) is a powerful tool for forging C(sp2)–C(sp2) bonds in biaryl molecules from abundant aromatic halides. While the synthesis of unsymmetrical biaryl compounds through multimetallic XEC is of high synthetic value, the selective XEC of two heteroaromatic halides remains elusive and challenging. Herein, we report a homogeneous XEC method, which relies on a zirconaaziridine complex as a shuttle for dual palladium-catalyzed processes. The zirconaaziridine-mediated palladium (ZAPd)-catalyzed reaction shows excellent compatibility with various functional groups and diverse heteroaromatic scaffolds. In accord with density functional theory (DFT) calculations, a redox transmetallation between the oxidative addition product and the zirconaaziridine is proposed as the crucial elementary step. Thus, cross-coupling selectivity using a single transition metal catalyst is controlled by the relative rate of oxidative addition of Pd(0) into the aromatic halide. Overall, the concept of a combined reducing and transmetallating agent offers opportunities for the development of transition metal reductive coupling catalysis.

Synthesis of dragmacidin D via direct C-H couplings

Dragmacidin D, an emerging biologically active marine natural product, has attracted attention as a lead compound for treating Parkinson's and Alzheimer's diseases. Prominent structural features of this compound are the two indole-pyrazinone bonds and the presence of a polar aminoimidazole unit. We have established a concise total synthesis of dragmacidin D using direct C-H coupling reactions. Methodological developments include (i) Pd-catalyzed thiophene-indole C-H/C-I coupling, (ii) Pd-catalyzed indole-pyrazine N-oxide C-H/C-H coupling, and (iii) acid-catalyzed indole-pyrazinone C-H/C-H coupling. These regioselective catalytic C-H couplings enabled us to rapidly assemble simple building blocks to construct the core structure of dragmacidin D in a step-economical fashion.