Catalyst control of selectivity in the C-O bond alumination of biomass derived furans.

ABSTRACT: Non-catalysed and catalysed reactions of aluminium reagents with furans, dihydrofurans and dihydropyrans were investigated and lead to ring-expanded products due to the insertion of the aluminium reagent into a C-O bond of the heterocycle. Specifically, the reaction of [{(ArNCMe)₂CH}Al] (Ar = 2,6-di-iso-propylphenyl, 1) with furans proceeded between 25 and 80 °C leading to dearomatised products due to the net transformation of a sp² C-O bond into a sp² C-Al bond. The kinetics of the reaction of 1 with furan were found to be 1st order with respect to 1 with activation parameters ΔH ^‡ = +19.7 (±2.7) kcal mol^-1, ΔS ^‡ = -18.8 (±7.8) cal K^-1 mol^-1 and ΔG ^‡

SUBMITTER: Hooper TN 

PROVIDER: S-EPMC8163288 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature