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Updated: Sep 23, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
A copper(ii)-catalyzed annulative formylation of o-alkynylanilines with DMF: a single-step strategy for 3-formyl
Balaji Ganesan1, Gopal Chandru Senadi1,2, Bing-Chun Guo1
1Department of Medicinal and Applied Chemistry, Kaohsiung Medical University No. 100 Shi-chuan, 1st Road Kaohsiung 807 Taiwan wylin@kmu.edu.tw.
Abstract:
In this paper, a copper(ii)-catalyzed reaction of o-alkynylanilines with dimethylformamide (DMF) in the presence of oxygen has been developed for synthesizing multisubstituted 3-formyl indole scaffolds. This one-pot reaction proceeds through a cascade 5-endo-dig cyclization followed by formylation to construct 1,2-disubstituted 3-formyl indoles. The key aspects of this synthesis method are the broad substrate scope (with 38 examples), and well tolerating various functional groups. In addition, a detailed mechanism has been proposed, where DMF may serve as a carbon source for the in situ C3 formylation of the obtained indole derivatives.
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