Highly selective α-aryloxyalkyl C–H functionalisation of aryl alkyl ethers† † Electronic supplementary information (ESI) available: Experimental procedures and supporting characterisation data are included. See DOI: https://doi.org/10.1039/d2sc04463c

ABSTRACT: We report highly selective photocatalytic functionalisations of alkyl groups in aryl alkyl ethers with a range of electron-poor alkenes using an acridinium catalyst with a phosphate base and irradiation with visible light (456 nm or 390 nm). Experiments indicate that the reaction operates via direct single-electron oxidation of the arene substrate ArOCHRR′ to its radical cation by the excited state organic photocatalyst; this is followed by deprotonation of the ArOC–H in the radical cation to yield the radical ArOC˙RR′. This radical then attacks the electrophile to form an intermediate alkyl radical that is reduced to complete the photocatalytic cycle. The oxidation step is selective for activated arenes (ArOR) over their non-activated counterparts and the subsequent deprotonation of the m

SUBMITTER: Bell J 

PROVIDER: S-EPMC9645420 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature