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Issue 100, 2018
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Copper-catalyzed, silver-mediated formal [3+2] cycloaddition of simple alkynes with β-ketoesters through propargylic C(sp3)–H functionalization

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Abstract

A copper-catalyzed propargylic [3+2] cycloaddition of simple alkynes with β-ketoesters through the propargylic C(sp3)–H functionalization has been realized. Under catalysis by CuI in combination with 1,10-phenanthroline hydrate as the ligand and Ag2CO3 as a bifunctional reagent (oxidant and base), the reaction proceeds smoothly with a broad substrate scope, thus providing a variety of highly functionalized furans in moderate to high yields. This represents the first successful example of the catalytic propargylic cycloaddition of simple alkynes with bisnucleophiles based on the propargylic C(sp3)–H functionalization strategy.

Graphical abstract: Copper-catalyzed, silver-mediated formal [3+2] cycloaddition of simple alkynes with β-ketoesters through propargylic C(sp3)–H functionalization

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Article information


Submitted
08 Oct 2018
Accepted
22 Nov 2018
First published
22 Nov 2018

Chem. Commun., 2018,54, 14100-14103
Article type
Communication

Copper-catalyzed, silver-mediated formal [3+2] cycloaddition of simple alkynes with β-ketoesters through propargylic C(sp3)–H functionalization

Z. Liu and X. Hu, Chem. Commun., 2018, 54, 14100
DOI: 10.1039/C8CC08013E

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