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Visible Light Photocatalytic Synthesis of Tetrahydroquinolines Under Batch and Flow Conditions

Daniel González‐Muñoz, José Luis Nova‐Fernández, Ada Martinelli, Gustavo Pascual‐Coca, Silvia Cabrera, José Alemán

2020European Journal of Organic Chemistry18 citationsDOI

Abstract

In this work, we describe the use of visible light and a photocatalytic system for the cyclization of iodoaryl vinyl derivatives to tetrahydroquinoline structures. The reaction proceeds under very mild conditions, tolerates different functional groups and more importantly, the method allows the synthesis of N ‐free tetrahydroquinolines from N ‐unprotected starting materials. In addition, the reaction can also be performed using flow‐chemistry. Finally, a mechanistic proposal based on some mechanistic studies has been described.

Topics & Concepts

ChemistryPhotocatalysisFlow chemistryVisible spectrumCombinatorial chemistryReaction mechanismReaction conditionsPhotochemistryContinuous flowOrganic chemistryCatalysisBiochemical engineeringEngineeringPhysicsOptoelectronicsInnovative Microfluidic and Catalytic Techniques InnovationRadical Photochemical ReactionsSulfur-Based Synthesis Techniques