Cu/SaBox-Catalyzed Photoinduced Coupling of Acylsilanes with Alkynes

Long Zheng; Xueying Guo; Ying-Chao Li; Yichen Wu; Xiao-Song Xue; Peng Wang

doi:10.1002/anie.202216373

Cu/SaBox-Catalyzed Photoinduced Coupling of Acylsilanes with Alkynes

Angew Chem Int Ed Engl. 2023 Jan 26;62(5):e202216373. doi: 10.1002/anie.202216373. Epub 2022 Dec 22.

Authors

Long Zheng^{1

2}, Xueying Guo³, Ying-Chao Li², Yichen Wu², Xiao-Song Xue^{1

3}, Peng Wang^{1

2

4}

Affiliations

¹ School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou, 310024, P. R. China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032, P. R. China.
³ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032, P. R. China.
⁴ CAS Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032, P. R. China.

PMID: 36465061
DOI: 10.1002/anie.202216373

Abstract

The transition metal-catalyzed cross-coupling reaction with Fischer metal carbene intermediates bearing an electron-rich alkoxyl or siloxyl group remains a big challenge due to the lack of readily available corresponding carbene precursors. Herein, we report the coupling of alkynes with the Fischer-type copper carbene species bearing a α-siloxyl group, which could be in situ generated from acylsilanes catalytically under photoirradiation and redox-neutral conditions. The side-arm modified bisoxazoline (SaBox) ligands prove to be crucial for this coupling reaction, which provides the corresponding alkynyl alcohol in high yields with remarkable heterocycle tolerance and broad substrate scope.

Keywords: Acylsilanes; Copper; Coupling Reaction; Fischer Carbene; Terminal Alkynes.

Abstract

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