Issue 3, 2020

Visible-light-driven spirocyclization of epoxides via dual titanocene and photoredox catalysis

Abstract

We describe the synergistic utilization of titanocene/photoredox dual catalysis driven by visible light for the radical opening/spirocyclization of easily accessible epoxyalkynes. This environmentally benign process uses the organic donor–acceptor fluorophore 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN) as a photocatalyst and Hantzsch ester (HE) as an electron donor instead of stoichiometric metallic reductants. The photocatalytic conditions showed exceptionally high reactivity for the synthesis of privileged and synthetically challenging spirocycles featuring a spiro all-carbon quaternary stereocenter. Cyclic voltammetry (CV) studies suggest that Cp2TiIIICl is the catalytically active species.

Graphical abstract: Visible-light-driven spirocyclization of epoxides via dual titanocene and photoredox catalysis

Supplementary files

Article information

Article type
Edge Article
Submitted
06 Nov 2019
Accepted
27 Nov 2019
First published
09 Dec 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 839-844

Visible-light-driven spirocyclization of epoxides via dual titanocene and photoredox catalysis

S. Lin, Y. Chen, F. Li, C. Shi and L. Shi, Chem. Sci., 2020, 11, 839 DOI: 10.1039/C9SC05601G

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