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A gold(i)-catalysed chemoselective three-component reaction between phenols, α-diazocarbonyl compounds and allenamides

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Abstract

Gold(I) catalysts are considered to be efficient in promoting sp2 C–H bond insertion at the para position of unprotected phenols because of the exceptionally chemical reactivity of gold-stabilized carbophilic carbocations. Herein, we present a gold(I)-catalysed three-component reaction between phenols, diazocarbonyl compounds and allenamides, affording the corresponding three-component reaction products with excellent geometric selectivity (E : Z > 20 : 1) in moderate to high yields (up to 90%) under mild conditions. Additionally, a gram-scale transformation and diverse transformations of the resulting product show the high synthetic utility of the present three-component protocol.

Graphical abstract: A gold(i)-catalysed chemoselective three-component reaction between phenols, α-diazocarbonyl compounds and allenamides

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Article information


Submitted
06 Dec 2019
Accepted
03 Jan 2020
First published
03 Jan 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

A gold(I)-catalysed chemoselective three-component reaction between phenols, α-diazocarbonyl compounds and allenamides

S. Yu, J. Chen, G. Liu, J. Lei, W. Hu and H. Qiu, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC09470A

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