Ligand-Enabled ortho-Selective C–H Olefination of Tertiary Aniline Derivatives

• DOI: 10.1021/acs.orglett.4c01315
• Publication Date: 2024-06-05T13:38:27Z
• Authors: Chunchen Yuan; Changbo Jia; Xinyu Zhang; Wenlong Zhang; Yang’en You; Xiaolong Xu; Lei Zhu; Yiliang Chen; Yongping Dong; Liang Xu

A highly ortho-selective CAr-H olefination of tertiary anilines without a directing group was developed. This reaction tolerated various substituted arenes and olefin coupling partners, affording ortho-olefination products in moderate to good yields. Preliminary mechanistic studies showed that N-Ac-d-Ala, Ag2CO3, and BQ were the key factors for tuning the regioselectivity from para to ortho. Density functional theory was used to achieve a theoretical understanding of the ortho selectivity.