Radical Cascade Multicomponent Minisci Reactions with Diazo Compounds

• DOI: 10.1021/acscatal.1c05611
• Publication Date: 2022-01-07T13:33:23Z
• Authors: Yong-Liang Su; Geng-Xin Liu; Luca De Angelis; Ru He; Ammar Al-Sayyed; Kirk S. Schanze; Wen-Hao Hu; Huang Qiu; Michael P. Doyle
• Keywords: Cascade reaction

Based on the strategy of polarity reversal in generation free radicals derived from diazo compounds, photocatalyzed multicomponent reactions (MCRs) nitrogen aromatic heterocycles, alkenes, and compounds form functionalized derivatives good to high yields exacting regioselectivities. The carbon generated acceptor are electrophilic, their selective additions with alkenes provide nucleophilic radicals, which enable further rapid assembly various heteroarenes. A delicate balance has been achieved between activation heteroarenes through protonation decomposition by same acid. This Minisci reaction shows functional group tolerance, especially incorporation biologically active molecules. Detailed mechanistic studies that include photophysical measurements elaborate this radical cascade reaction. Furthermore, transformation provides new opportunities for versatile coupling reactions.