Gold-Catalyzed syn-1,2-Difunctionalization of Ynamides via Nitrile Activation

• DOI: 10.1021/acs.orglett.8b03830
• Publication Date: 2018-12-12T15:22:15Z
• Authors: Rajeshwer Vanjari; Shubham Dutta; Manash P. Gogoi; Vincent Gandon; Akhila K. Sahoo
• Keywords: [CHIM.OTHE]Chemical Sciences/Other; 01 natural sciences; 0104 chemical sciences

Developed is an unprecedented Au(I)-catalyzed syn-1,2-difunctionalization of ynamides with 2-aminobenzonitriles via nitrile activation. The coupling between and explicitly regioselective, providing a straightforward access to 2,4-diamino-substituted quinolines. Density functional theory (DFT) study provides insightful information rationalizes the reaction pathway. It shows how synergy ynamide π-activation σ-coordination by Au(I) catalyst makes cyclization viable.