Palladium-catalyzed β-C(sp³)-H biarylation using native directing groups

Chotia, Mohit (2022) Palladium-catalyzed β-C(sp³)-H biarylation using native directing groups. Masters thesis, Indian Institute of Science Education and Research Kolkata.

Text (MS dissertation of Mohit Chotia (17MS218)) 17MS218_Thesis_file.pdf - Submitted Version Restricted to Repository staff only Download (4MB)

Abstract

Achieving site-selective C(sp³)-H bond activation has always been considered a leading challenge in modern organometallic chemistry. In recent times, one such challenge is achieving site-selective C(sp³)-H bond activation using native directing groups to overcome the drawbacks imposed by the use of strong coordinating traditional N-coordinationbased directing groups. The synthesis of biaryl motifs, an important class of biologically active molecules, has always been complex. It is always desirable to overcome this with a single-pot strategy and make it a step-economical process. Herein, we report the first-ever β-C(sp³)-H bond activation of aliphatic or aromatic amides via the native directing group strategy using hypervalent cyclic diaryliodonium salts. The reaction was catalyzed by palladium acetate in the presence of pyridine-3- sulfonic acid as a ligand. It showed decent substrate scope. However, further substrate exploration is necessary.

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