Intermolecular [3+2] Annulation of Cyclopropylanilines with Alkynes, Enynes, and Diynes via Visible Light Photocatalysis

• Published in: Advanced synthesis & catalysis Vol. 356; no. 13; pp. 2831 - 2837
• Main Authors: Nguyen, Theresa H., Morris, Scott A., Zheng, Nan
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 15.09.2014; WILEY‐VCH Verlag; Wiley
• Subjects: [3+2] annulation; Alkenes; Alkynes; Amines; Catalysis; Chemical reactions; Chemistry; Chemistry, Applied; Chemistry, Organic; cyclopropylanilines; diynes; enynes; intermolecular annulation; Organic chemistry; Photocatalysis; Physical Sciences; Science & Technology; Synthesis; visible light; alkynes; COMPLEXES; [3+2] annulation; cyclopropylanilines; visible light; DEPROTECTION; diynes; enynes; photocatalysis; intermolecular annulation; PHOTOREDOX CATALYSIS; intermolecular
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201400742

One‐step syntheses of carbocycles substituted with amines from simple starting materials remain rare. We recently developed an intermolecular [3+2] annulation of cyclopropylanilines with alkenes and alkynes that enables this one‐step synthesis. Herein, we report our findings for a full‐scale study of the annulation. Significant expansion of the substrate scope for both cyclopropylanilines and alkynes has been achieved. A range of structurally diverse carbocycles substituted with amines is prepared.