An unprecedented palladium-arsenic catalytic cycle for nitriles hydration

Damiano Cirri; Tiziano Marzo; Alessandro Pratesi

doi:10.3389/fchem.2023.1253008

An unprecedented palladium-arsenic catalytic cycle for nitriles hydration

Front Chem. 2023 Aug 7:11:1253008. doi: 10.3389/fchem.2023.1253008. eCollection 2023.

Authors

Damiano Cirri¹, Tiziano Marzo², Alessandro Pratesi¹

Affiliations

¹ Department of Chemistry and Industrial Chemistry, University of Pisa, Pisa, Italy.
² Department of Pharmacy, University of Pisa, Pisa, Italy.

Abstract

An unprecedented palladium/arsenic-based catalytic cycle for the hydration of nitriles to the corresponding amides is here described. It occurs in exceptionally mild conditions such as neutral pH and moderate temperature (60°C). The versatility of this new catalytic cycle was tested on various nitriles from aliphatic to aromatic. Also, the effect of ring substitution with electron withdrawing and electron donating groups was investigated in the cases of aromatic nitriles, as well as the effect of potentially interferent functional groups such as hydroxy group or pyridinic nitrogen. Furthermore, a pilot study on the potential suitability of this approach for its scale-up is presented, revealing that the catalytic cycle could be potentially and quickly scaled up.

Keywords: amide synthesis; arsenic catalysis; heterobimetallic catalysis; nitrile hydration; palladium catalysis.

Grants and funding

AP gratefully acknowledges funding by the University of Pisa under the “PRA-Progetti di Ricerca di Ateneo” (Institutional Research Grants), project no. PRA_2022-2023_12 “New challenges of transition metal and lanthanide complexes in the perspective of green chemistry”; TM thanks the University of Pisa (Fondi di Ateneo 2020-2021 and PRA_2020_58).