Abstract
The conservation of our global element resources is a challenge of the utmost urgency. Since aliphatic and aromatic alcohols are accessible from abundant indigestible kinds of biomass, first and foremost lignocellulose, the development of novel chemical reactions converting alcohols into important classes of compounds is a particularly attractive carbon conservation and CO2-emission reduction strategy. Herein, we report the catalytic condensation of phenols and aminophenols or aminoalcohols. The overall reaction of this synthesis concept proceeds via three steps: hydrogenation, dehydrogenative condensation and dehydrogenation. Reusable catalysts recently developed in our laboratory mediate these reactions highly efficient. The scope of the concept is exemplarily demonstrated by the synthesis of carbazoles, quinolines and acridines, the structural motifs of which figure prominently in many important natural products, drugs and materials.
Highlights
The conservation of our global element resources is a challenge of the utmost urgency
We used Ir catalysts introduced by our group recently; preferentially a reusable Ir@silicon carbonitride (SiCN) catalyst[8] or a PN5Ppincer catalysts[3] if its performance was significantly better for a certain combination of starting materials
We expect the catalytic condensation introduced here to become an integral part of the new alcohol based sustainable chemistry that permits the catalytic synthesis of organic compounds from aliphatic and/or aromatic alcohols
Summary
The conservation of our global element resources is a challenge of the utmost urgency. A concept has been introduced recently by which the combination of dehydrogenation and condensation steps permits the synthesis of important aromatic N-heterocycles, such as pyrroles[3,4,5,6,7,8,9], pyridines[10,11,12,13], and pyrimidines[14,15,16], starting from aliphatic alcohols (Fig. 1a)[17, 18]. We report on a concept of a sustainable synthesis in which phenols and aminophenols or aminoalcohols undergo a catalytic condensation reaction for the formation of polycyclic Nheteroaromatic compounds (Fig. 1b). The target polycyclic aromatic N-heterocycles have a wide range of conceivable applications in medicine and materials science
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