1365092-36-9

Upstream product

• 5390-04-5 pent-1-yn-5-ol 
• 637-87-6 1-Chloro-4-iodobenzene 
• 138487-22-6 5-(4-chlorophenyl)-4-pentyn-1-ol 

Downstream Products

• 1311380-67-2 C₂₁H₁₇Cl₂NO 
• 1311380-58-1 C₂₀H₁₅Cl₂NO 
• 1352998-10-7 3,5-dichloro-1-(5-(4-chlorophenyl)pent-4-ynyl)pyrrole-2,4-dicarbaldehyde 

Relevant academic research and scientific papers

Palladium/Norbornene-Catalyzed C?H Alkylation/Alkyne Insertion/Indole Dearomatization Domino Reaction: Assembly of Spiroindolenine-Containing Pentacyclic Frameworks

Reported is a highly chemoselective intermolecular annulation of indole-based biaryls with bromoalkyl alkynes by using palladium/norbornene (Pd/NBE) cooperative catalysis. This reaction is realized through a sequence of Catellani-type C?H alkylation, alkyne insertion, and indole dearomatization, by forming two C(sp2)?C(sp3) and one C(sp2)?C(sp2) bonds in a single chemical operation, thus providing a diverse range of pentacyclic molecules, containing a spiroindolenine fragment, in good yields with excellent functional-group tolerance. Preliminary mechanistic studies reveal that C?H bond cleavage is likely involved in the rate-determining step, and the indole dearomatization might take place through an olefin coordination/insertion and β-hydride elimination Heck-type pathway.