Abstract
Transformation of aryl alcohols into high-value functionalized aromatic compounds by selective cleavage and functionalization of the C(aryl)–C(OH) bond is of crucial importance, but very challenging by far. Herein, for the first time, we report a novel and versatile strategy for activation and functionalization of C(aryl)–C(OH) bonds by the cooperation of oxygenation and decarboxylative functionalization. A diverse range of aryl alcohol substrates were employed as arylation reagents via the cleavage of C(aryl)–C(OH) bonds and effectively converted into corresponding thioether, arene, and arylated benzoxazole products in excellent yields, in a Cu based catalytic system using O2 as the oxidant. This study offers a new way for aryl alcohol conversion and potentially offers a new opportunity to produce high-value functionalized aromatics from renewable feedstocks such as lignin which features abundant C(aryl)–C(OH) bonds in its linkages.
Highlights
Functionalized aromatic compounds are ubiquitously involved in and of signi cant importance in medicinal chemistry, biological chemistry and the chemical industry
A diverse range of aryl alcohol substrates were employed as arylation reagents via the cleavage of C(aryl)–C(OH) bonds and effectively converted into corresponding thioether, arene, and arylated benzoxazole products in excellent yields, in a Cu based catalytic system using O2 as the oxidant
We started our study about C(aryl)–C(OH) bond activation and functionalization by oxidative thioetheri cation using a secondary aryl alcohol 1-(2-nitrophenyl)ethanol (1a) as a model substrate, in a catalytic reaction system consisting of diphenyldisulfane (2a) as the sulfur source, CuSO4 as the catalyst, 1,10-phenanthroline as the ligand, K2CO3 as a base additive, DMSO as the solvent and O2 as the environmentally benign oxidant (Table 1)
Summary
Functionalized aromatic compounds are ubiquitously involved in and of signi cant importance in medicinal chemistry, biological chemistry and the chemical industry. Expensive pre-functionalized aromatic substrates originating from nite and depleting fossil resources, such as aryl halides,[6] aniline/thiophenol/phenol derivatives[7,8,9,10,11,12,13,14,15] and aryl compounds,[16,17,18,19,20,21,22,23,24,25] are almost exclusively used as feedstocks. Cross-coupling reactions suffer from some drawbacks such as low atom economy, requirement for sophisticated catalysts or catalytic systems, generation and inevitable handling of toxic and corrosive halide-containing
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