Chemo-, regio- and stereoselective access to polysubstituted 1,3-dienes via Nickel-catalyzed four-component reactions

Shanglin Chen, Ya-Nan Wang, Jinhui Xie, Wangyang Li, Mingxing Ye, Xingxing Ma, Kai Yang, Shijun Li, Yu Lan () and Qiuling Song ()
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Shanglin Chen: College of Chemistry at Fuzhou University
Ya-Nan Wang: Chongqing University
Jinhui Xie: College of Chemistry at Fuzhou University
Wangyang Li: College of Chemistry at Fuzhou University
Mingxing Ye: College of Chemistry at Fuzhou University
Xingxing Ma: College of Chemistry at Fuzhou University
Kai Yang: College of Chemistry at Fuzhou University
Shijun Li: Zhengzhou University
Yu Lan: Chongqing University
Qiuling Song: College of Chemistry at Fuzhou University

Nature Communications, 2024, vol. 15, issue 1, 1-14

Abstract: Abstract 1,2-Difunctionalization of alkynes offers a straightforward approach to access polysubstituted alkenes. However, simultaneous multi-component cascade transformations including difunctionalization of two alkynes with both syn- and anti-selectivity in one catalyst system is undeveloped and proves to be a significant challenge. Herein, we report a Nickel-catalyzed four-component reaction to access polysubstituted 1,3-dienes using two terminal alkynes, aryl boroxines, and perfluoroalkyl iodides, wherein the reaction forms three new C-C bonds in a single vessel and serve as a modular strategy to access polysubstituted 1,3-dienes with excellent chemoselectivity, good regioselectivity and exclusive stereoselectivity. Control experiments reveal the plausible reaction mechanism and DFT calculations explain the cause for the formation of this unusual four-component reaction. Furthermore, we successfully incorporate two biologically active units into 1,2,3,4-tetrasubstituted 1,3-dienes, which greatly increases the diversity of molecular scaffolds and brings more potential values to medicinal chemistry, the synthetic utility of our protocol is further demonstrated by the late-stage transformations.

Date: 2024
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DOI: 10.1038/s41467-024-49870-1

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