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Visible Light Driven Photocascade Catalysis: Ru(bpy)3(PF6)2/TBHP-Mediated Synthesis of Fused β-Carbolines in Batch

D Chandrasekhar, Satheesh Borra, Jagadeesh Babu Nanubolu

¹Chemical Science and Technology Division, CSIR-North East Institute of Science and Technology , Jorhat, Assam 785006, India.

Organic Letters

|May 27, 2016

Abstract:

1,2,3,4-Tetrahydro-β-carbolines were coupled with α-keto vinyl azides through an unprecedented visible light-Ru(bpy)3(PF6)2/TBHP mediated photocascade strategy that involves photosensitization, photoredox catalysis and [3 + 2] cycloaddition reaction. The scope and scale-up feasibility of the photocascade strategy was demonstrated by synthesizing 18 different fused β-carbolines in moderate to good yields using batch and continuous flow microreactor. This operationally simple synthetic protocol allows the formation of one C-C and two C-N new bonds in the overall transformation.

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