Regioselectively Functionalized Pyridines from Sustainable Resources

Abstract

Make the most of it! An Ir‐catalyzed dehydrogenative condensation of alcohols and 1,3‐amino alcohol was used to construct pyridine derivatives regioselectively. This method provides access to unsymmetrically substituted pyridines and tolerates a wide variety of functional groups. Three equivalents of H2 are generated per pyridine unit formed and the alcohol substrates become completely deoxygenated.

A Highly Active and Easily Accessible Cobalt Catalyst for Selective Hydrogenation of C═O Bonds

“…11 Haupt and coworker introduced such PN3P ligands 12 and Kirchner and coworker have demonstrated the broad applicability of the ligand class. 13 Reports on cobalt complexes stabilized by such ligands are rare.…”

Synthese meta‐funktionalisierter Pyridine über selektive dehydrierende Heterokondensation von β‐ und γ‐Aminoalkoholen

“…[1] Solche neuartigen Reaktionen sind besonders vielversprechend, wenn bestehende Synthesemethoden signifikant erweitert werden. [1,[3][4][5] Wirh aben zur Entwicklung beider Konzepte beigetragen [1,4,6] und berichten hier über die Synthese von 3-Aminopyridinen durch Kombinieren von BH/HA und ADC.D iole werden mit Aminen katalytisch zu b-Aminoalkoholen um-gesetzt, die anschließend mit g-Aminoalkoholen eine selektive dehydrierende Heterokondensation durchlaufen. [2,3] Im Zusammenhang damit steht die Kombination von katalytischer Dehydrierung und Kondensation, die akzeptorlose dehydrierende Kondensation (ADC), die die Synthese von aromatischen N-heterocyclischen Verbindungen aus Alkoholen ermçglicht.…”

Synthesis of meta‐Functionalized Pyridines by Selective Dehydrogenative Heterocondensation of β‐ and γ‐Amino Alcohols

“…[2,3] Related to this is the combination of catalytic dehydrogenation and condensation in acceptorless dehydrogenative condensation (ADC), which enables the synthesis of aromatic N-heterocyclic compounds from alcohols. [1,[3][4][5] We have contributed to the development of both concepts [1,4,6] and herein report on the synthesis of 3-aminopyridines by combining BH/HA and ADC. Diols are catalytically reacted with amines to form b-amino alcohols, which then underwent a highly selective dehydrogenative heterocondensation with g-amino alcohols.…”

“…Iridium catalysts stabilized by PN 5 P pincer ligands that were developed in our laboratory mediate this reaction selectively and most efficiently. [4] The problems associated with the synthesis of 3-aminopyridines [7] and the degree of novelty of the catalytic synthesis discussed here are also expressed by the fact that all examples that we have catalytically synthesized are novel compounds. The privileged pyridine motif is found in many natural products, bioactive molecules, agrochemicals, pharmaceuticals, and functional materials.…”