Integrating Biomass into the Organonitrogen Chemical Supply Chain: Production of Pyrrole and <scp>d</scp>‐Proline from Furfural

Song Song, Vincent Fung Kin Yuen, Lu Di, Qiming Sun, Kang Zhou, Ning Yan

Angewandte Chemie International Edition · 2020 · 124 citations · 36 references

Concepts

Abstract

Abstract Production of renewable, high‐value N‐containing chemicals from lignocellulose will expand product diversity and increase the economic competitiveness of the biorefinery. Herein, we report a single‐step conversion of furfural to pyrrole in 75 % yield as a key N‐containing building block, achieved via tandem decarbonylation–amination reactions over tailor‐designed Pd@S‐1 and H‐beta zeolite catalytic system. Pyrrole was further transformed into dl ‐proline in two steps following carboxylation with CO 2 and hydrogenation over Rh/C catalyst. After treating with Escherichia coli, valuable d ‐proline was obtained in theoretically maximum yield (50 %) bearing 99 % ee. The report here establishes a route bridging commercial commodity feedstock from biomass with high‐value organonitrogen chemicals through pyrrole as a hub molecule.

References

36