Work

Formate-Mediated C–C Coupling of Aryl/Vinyl Halides and Triflates: Carbonyl Arylation and Reductive Cross-Coupling

Year: 2025

Type: article

Abstract: Catalytic methods for the intermolecular formate-mediated C–C coupling of Csp 2 -X pronucleophiles beyond reductive Heck reactions (alkene hydroarylations) are catalogued. These methods include transfer hydrogenative reductive couplings of aryl/vinyl halides or triflates to carbonyl compounds (Grignard/NHK-type reactions) as well as reductive cross-couplings of two aryl/vinyl halide or triflate partners. These studies demonstrate that reactions traditionally associated with discrete Csp 2 carbanions can be rendered catalytic and free from premetalated reagents or zerovalent metals using sodium or potassium formate, which are abundant, safe, low molecular weight reductants.

Source: ACS Catalysis

DOI: 10.1021/acscatal.5c01994

Authors: Yu-Hsiang Chang, Yoon Cho, Weijia Shen, Michael J. Krische

Institution: The University of Texas at Austin

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Welch Foundation, National Institute of General Medical Sciences

Awards: G3277079756, G7991472476