Iridium-Catalyzed Aerobic Coupling of Salicylaldehydes with Alkynes: A Remarkable Switch of Oxacyclic Product.
Shintaro YamaneTomoaki HinoueYoshinosuke UsukiMasumi ItazakiHiroshi NakazawaYoshihiro HayashiSusumu KawauchiMasahiro MiuraTetsuya SatohPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2018)
The iridium(III)/copper(II)-catalyzed dehydrogenative coupling of salicylaldehydes with internal alkynes proceeds efficiently under atmospheric oxygen through aldehyde C-H bond cleavage and decarbonylation. A variety of benzofuran derivatives can be synthesized by the environmentally benign procedure. DFT calculations suggest that this unique transformation involves the facile deinsertion of CO in the key metallacycle intermediate, which is in marked contrast to the corresponding rhodium(III) catalysis that leads to CO-retentive chromone derivatives.
Keyphrases
- room temperature
- density functional theory
- ionic liquid
- magnetic resonance
- oxide nanoparticles
- molecular dynamics
- structure activity relationship
- visible light
- molecular dynamics simulations
- particulate matter
- molecular docking
- high intensity
- quantum dots
- magnetic resonance imaging
- reduced graphene oxide
- computed tomography
- air pollution