Gold-catalyzed four-component multifunctionalization of alkynes

Shangwen Fang, Jie Han, Chengjian Zhu, Weipeng Li and Jin Xie ()
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Shangwen Fang: Nanjing University
Jie Han: Nanjing University
Chengjian Zhu: Nanjing University
Weipeng Li: Nanjing University
Jin Xie: Nanjing University

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract The alkyne unit is a versatile building block in organic synthesis and the development of selective multifunctionalization of alkynes is an important object of research in this field. Herein, we report an interesting gold-catalyzed, four-component reaction that achieves the oxo-arylfluorination or oxo-arylalkenylation of internal aromatic or aliphatic alkynes, efficiently breaking a carbon-carbon triple bond and forming four new chemical bonds. The reaction divergence can be controlled by site-directing functional groups in the alkynes; the presence of a phosphonate unit favors the oxo-arylfluorination, while the carboxylate motif benefits oxo-arylalkenylation. This reaction is enabled by an Au(I)/Au(III) redox coupling process using Selectfluor as both an oxidant and a fluorinating reagent. A wide range of structurally diverse α,α-disubstituted ketones, and tri- or tetra-substituted unsaturated ketones have been prepared in synthetically valuable yields and with excellent chemo-, regio- and stereoselectivity. The gram-scale preparation and late-stage application of complex alkynes have further enhanced their synthetic value.

Date: 2023
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DOI: 10.1038/s41467-023-39243-5

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