Gawali, Suhas Shahaji; Pandia, Biplab Keshari; Pal, Souvik; Gunanathan, Chidambaram published the artcile< Manganese(I)-Catalyzed Cross-Coupling of Ketones and Secondary Alcohols with Primary Alcohols>, Product Details of C8H9FO, the main research area is cross coupling manganese catalyzed ketone primary alc.
Catalytic cross-coupling of ketones and secondary alcs. with primary alcs. is reported. An abundant manganese based pincer catalyst catalyzes the reactions. Low loading of catalyst (2 mol %) and catalytic use of a mild base (5-10 mol %) are sufficient for efficient cross-coupling. Various aryl and heteroaryl ketones are catalytically cross-coupled with primary alcs. to provide the selective α-alkylated products. Challenging α-ethylation of ketones is also attained using ethanol as an alkylating reagent. Further, direct use of secondary alcs. in the reaction results in in situ oxidation to provide the ketone intermediates, which undergo selective α-alkylation. The reaction proceeds via the borrowing hydrogen pathway. The catalyst oxidizes the primary alcs. to aldehydes, which undergo subsequent aldol condensation with ketones, promoted by catalytic amount of Cs2CO3, to provide the α,β-unsaturated ketone intermediates. The hydrogen liberated from oxidation of alcs. is used for hydrogenation of α,β-unsaturated ketone intermediates. Notably either water or water and dihydrogen are the only byproducts in these environmentally benign catalytic processes. Mechanistic studies allowed inferring all the intermediates involved. Dearomatization-aromatization metal-ligand cooperation in the catalyst facilitates the facile O-H bond activation of both primary and secondary alcs. and the resultant manganese alkoxide complexes produce corresponding carbonyl compounds, perhaps via β-hydride elimination. The manganese(I) hydride intermediate plays dual role as it hydrogenates α,β-unsaturated ketones and liberates mol. hydrogen to regenerate the catalytically active dearomatized intermediate. Metal-ligand cooperation allows all the manganese intermediate to exist in same oxidation state (+1) and plays an important role in these catalytic cross-coupling reactions.
ACS Omega published new progress about Cross-coupling reaction. 403-41-8 belongs to class alcohols-buliding-blocks, and the molecular formula is C8H9FO, Product Details of C8H9FO.
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts