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Issue 14, 2019
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A photoinduced Wolff rearrangement/Pd-catalyzed [3+2] cycloaddition sequence: an unexpected route to tetrahydrofurans

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Abstract

A novel sequential reaction that combines a visible light-induced Wolff rearrangement of α-diazoketones and a Pd-catalyzed [3+2] cycloaddition of vinyl cyclopropanes with the resulting ketenes is described in this work. Selective O-allylic alkylation was observed over C-allylic alkylation, which unexpectedly led to a series of highly functionalized tetrahydrofurans with high efficiency (20 examples, 58–99% yields).

Graphical abstract: A photoinduced Wolff rearrangement/Pd-catalyzed [3+2] cycloaddition sequence: an unexpected route to tetrahydrofurans

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Supplementary files

Article information


Submitted
23 Dec 2018
Accepted
21 Jan 2019
First published
22 Jan 2019

Chem. Commun., 2019,55, 2031-2034
Article type
Communication

A photoinduced Wolff rearrangement/Pd-catalyzed [3+2] cycloaddition sequence: an unexpected route to tetrahydrofurans

J. Liu, M. Li, B. Qu, L. Lu and W. Xiao, Chem. Commun., 2019, 55, 2031
DOI: 10.1039/C8CC10157D

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