Work

Redox‐Neutral Vicinal Dialkylation of Aryl Boronic Esters via the Palladium/Norbornene Cooperative Catalysis

Year: 2026

Type: article

Abstract: ABSTRACT Palladium/norbornene (Pd/NBE) cooperative catalysis has become an increasingly important tool for ipso/ortho difunctionalization of arenes; however, the ipso functionalization is primarily limited to coupling of a nucleophile or a π‐system. Here, we report a new type of Pd/NBE‐catalyzed difunctionalization reaction that simultaneously couples two alkyl electrophiles at the ipso and ortho positions of arenes. Diverse aryl boronic esters are employed as substrates. The redox‐neutral feature of this reaction allows broad functional group tolerance. The synthetic utility is demonstrated in a streamlined preparation of a complex benzoazepane. Mechanistic studies reveal the potential involvement of an unusual radical‐mediated ipso functionalization.

Source: Angewandte Chemie

DOI: 10.1002/ange.2236309

Authors: Rong Ye, Peimiao He, Liyan Kan, Thomas R. Plambeck, Guangbin Dong

Institution: University of Chicago

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,790

Funders: University of Chicago, National Institute of General Medical Sciences