祝贺贾欢欢研究成果发表在JACS上

Reductive Coupling of N-Heteroarenes and 1,2-Dicarbonyls for Direct Access to γ-Amino Acids, Esters, and Ketones Using a Heterogeneous Single-Atom Iridium Catalyst

Huanhuan Jia,¹ Qi Liao,¹ Wei Liu,¹ Luis A. Cipriano,² Huanfeng Jiang,¹ Pierre. H. Dixneuf,³ Gianvito Vilé,² Min Zhang^1,*

Abstract: Despite their significant importance, the challenges in direct and diverse synthesis of N-heterocyclic γ-amino acids/esters/ketones hamper exploring their applications. Herein, by developing a multifunctional heterogeneous iridium single-atom catalyst composing of silica-confined iridium species and boron-doped ZrO₂ support (Ir-SAs@B-ZrO₂/SiO₂), we describe its utility in establishing a new reductive coupling reaction of N-heteroarenes and 1,2-dicarbonyls for selective and diverse construction of the as-described compounds in a straightforward manner. The striking features, including good substrate and functionality tolerance, high step and atom economy, exceptional catalyst reusability, and diversified product post-transformations, highlight the practicality of the developed chemistry. Mechanistic studies reveal that the synergy between the active Ir-sites and acidic support favors a chemo-selective reduction of the more inert N-heteroarenes and affords requisite enamine intermediates. In this work, the concept on precise transformation of reductive intermediates will open a door to further develop useful tandem reactions by rational catalyst design.

J. Am. Chem. Soc., 2024, 146, Doi: org/10.1021/jacs.4c09827