Base-Selective Five- versus Six-Membered Ring Annulation in Palladium-Catalyzed C-C Coupling Cascade Reactions: New Access to Electron-Poor Polycyclic Aromatic Dicarboximides

2017 ◽  
Vol 56 (26) ◽  
pp. 7595-7600 ◽  
Author(s):  
Sabine Seifert ◽  
David Schmidt ◽  
Kazutaka Shoyama ◽  
Frank Würthner
Keyword(s):  
Cascade Reactions ◽  
Membered Ring ◽  
Polycyclic Aromatic ◽  
Palladium Catalyzed

scholarly journals How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C10H7) to benzindenes (C13H10) as a case study

2019 ◽  
Vol 21 (30) ◽  
pp. 16737-16750 ◽  
Author(s):  
Long Zhao ◽  
Matthew Prendergast ◽  
Ralf I. Kaiser ◽  
Bo Xu ◽  
Utuq Ablikim ◽  
...  
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Molecular Mass ◽  
Aromatic Hydrocarbons ◽  
Membered Ring ◽  
Growth Processes ◽  
Mass Growth ◽  
Aryl Radicals ◽  
Polycyclic Aromatic

The reaction of aryl radicals with allene/methylacetylene leads to five-membered ring addition in PAH growth processes.

Palladium-Catalyzed Cascade Reactions of Isocyanides with Enaminones: Synthesis of 4-Aminoquinoline Derivatives

ACS Catalysis ◽  
2013 ◽  
Vol 4 (1) ◽  
pp. 49-52 ◽  
Author(s):  
Zheng-Yang Gu ◽  
Tong-Hao Zhu ◽  
Jia-Jia Cao ◽  
Xiao-Ping Xu ◽  
Shun-Yi Wang ◽  
...  
Keyword(s):  
Cascade Reactions ◽  
Palladium Catalyzed

Palladium-Catalyzed Coupling Reaction of 3-Bromo Benzo[b]furan, -thiophene and -selenophene 2-Carboxaldehyde. Preparation of Tetracyclic Heteroaromatic Derivatives

2006 ◽  
Vol 61 (4) ◽  
pp. 427-430 ◽  
Author(s):  
Gilbert Kirsch ◽  
Stéphanie Deprets
Keyword(s):  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Polycyclic Aromatic ◽  
Palladium Catalyzed

3-Oxo-2,3-dihydrobenzo[b]furans, -thiophenes and -selenophenes 1a - c afforded the bromo-aldehydes 2 under Vilsmeier-Haack-Arnold conditions. Palladium-catalysed aryl-aryl coupling of 2 with o-formyl-phenylboronic acid allowed the formation of dialdehydes 3 which underwent McMurry cyclisation or pinacol condensation to yield polycyclic aromatic derivatives 4 or the dihydroxylated compounds 5

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