Palladium/Copper-Cocatalyzed Arylsilylation of Internal Alkynes with Acyl Fluorides and Silylboranes: Synthesis of Tetrasubstituted Alkenylsilanes by Three-Component Coupling Reaction

Qiang Chen; Zhenyao Li; Yasushi Nishihara

doi:10.1021/acs.orglett.1c04060

Palladium/Copper-Cocatalyzed Arylsilylation of Internal Alkynes with Acyl Fluorides and Silylboranes: Synthesis of Tetrasubstituted Alkenylsilanes by Three-Component Coupling Reaction

Org Lett. 2022 Jan 14;24(1):385-389. doi: 10.1021/acs.orglett.1c04060. Epub 2021 Dec 22.

Authors

Qiang Chen¹, Zhenyao Li¹, Yasushi Nishihara²

Affiliations

¹ Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan.
² Research Institute for Interdisciplinary Science, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan.

PMID: 34936358
DOI: 10.1021/acs.orglett.1c04060

Abstract

In this Letter, the palladium/copper-cocatalyzed arylsilylation of internal alkynes with acyl fluorides and silylboranes is described. This is the first example in which acyl fluorides have been utilized for the three-component coupling reaction via decarbonylation, yielding a variety of tetrasubstituted alkenylsilanes in moderate to good yields.