Rhodium-Catalyzed Tandem Reaction of N-(Pivaloyloxy)acrylamides with 1,3-Diynes for the Synthesis of Furo[2,3-b]pyridines

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 19, 2025

We disclose a rhodium-catalyzed tandem reaction of N-(pivaloyloxy)acrylamides with 1,3-diynes for the efficient synthesis furo[2,3-b]pyridines. This unique includes C-H activation, Lossen rearrangement, [4+2] annulation, and [3+2] annulation in "one pot", which features readily available substrates, broad functional group compatibility, ability to isolate pure products through simple filtration under ambient conditions excellent regioselectivity, selectivity mono- or diannulation, intra- intermolecular selectivity. Furthermore, this synthetic protocol facilitates rapid construction diverse library blue-emitting molecules high quantum yields, providing valuable platform developing advanced materials.

Language: Английский

DFT Investigation on Palladium-Catalyzed [2 + 2 + 1] Spiroannulation between Aryl Halides and Alkynes: Mechanism, Base Additive Role, and Solvent and Ligand Effects

The Journal of Physical Chemistry A, Journal Year: 2024, Volume and Issue: 128(42), P. 9135 - 9145

Published: Oct. 11, 2024

Transition metal-catalyzed spiroannulations are practical strategies for constructing spirocyclic skeletons of pharmaceutical and biological significance, yet the microscopic mechanism still lacks in-depth explorations. Here, palladium-catalyzed [2 + 2 1] spiroannulation between aryl halides alkynes was studied by employing density functional theory (DFT) method. Based on comprehensive explorations a couple possible reaction pathways, it is found that probably experiences C-I oxidative addition, alkyne migration insertion, Cs

Language: Английский