Issue 35, 2017

Visible light catalyzed Mannich reaction between tert-amines and silyl diazoenolates

Abstract

The present work documents the α-C–H functionalization of tertiary amines via the visible light catalyzed Mannich reaction with silyl diazoenolates. The reaction takes place at room temperature with an organic dye, Rose Bengal, as a photocatalyst and oxygen as the oxidant. The resulting multifunctional products bearing an α-diazo-β-keto group undergo Rh-carbenoid mediated cyclization, affording stable ammonium ylides in high yields.

Graphical abstract: Visible light catalyzed Mannich reaction between tert-amines and silyl diazoenolates

Supplementary files

Article information

Article type
Paper
Submitted
17 Jul 2017
Accepted
15 Aug 2017
First published
22 Aug 2017

Org. Biomol. Chem., 2017,15, 7369-7373

Visible light catalyzed Mannich reaction between tert-amines and silyl diazoenolates

M. M. D. Pramanik, S. B. Nagode, R. Kant and N. Rastogi, Org. Biomol. Chem., 2017, 15, 7369 DOI: 10.1039/C7OB01756A

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