Alumination of aryl methyl ethers: switching between sp2 and sp3 C–O bond functionalisation with Pd-catalysis. Issue 88 (21st October 2021)

• Record Type: Journal Article
• Authors: Brown, Ryan K.; Hooper, Thomas N.; Rekhroukh, Feriel; White, Andrew J. P.; Costa, Paulo J.; Crimmin, Mark R.
• Is Part Of: Chemical communications. Volume 57:Issue 88(2021)
• Page Start: 11673
• Page End: 11676
• Publication Date: 2021-10-21
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc05408b
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : The selectivity of the reaction of a low-valent aluminium reagent with aryl methyl ethers can be controlled by a catalyst. Abstract : The reaction of [{(ArNCMe)2 CH}Al] (Ar = 2, 6-di-iso-propylphenyl) with aryl methyl ethers proceeded with alumination of the sp 3 C–O bond. The selectivity of this reaction could be switched by inclusion of a catalyst. In the presence of [Pd(PCy3 )2 ], chemoselective sp 2 C–O bond functionalisation was observed. Kinetic isotope experiments and DFT calculations support a catalytic pathway involving the ligand-assisted oxidative addition of the sp 2 C–O bond to a Pd–Al intermetallic complex.