Pathway-divergent coupling of 1,3-enynes with acrylates through cascade cobalt catalysis

Heng Wang; Xiaofeng Jie; Qinglei Chong; Fanke Meng

doi:10.1038/s41467-024-47719-1

Pathway-divergent coupling of 1,3-enynes with acrylates through cascade cobalt catalysis

Nat Commun. 2024 Apr 23;15(1):3427. doi: 10.1038/s41467-024-47719-1.

Authors

Heng Wang¹, Xiaofeng Jie¹, Qinglei Chong², Fanke Meng^{3

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Affiliations

¹ State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
² State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. chongql@sioc.ac.cn.
³ State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. mengf@sioc.ac.cn.
⁴ State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300074, China. mengf@sioc.ac.cn.
⁵ School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou, 310024, China. mengf@sioc.ac.cn.
⁶ Beijing National Laboratory for Molecular Sciences, Beijing, 100086, China. mengf@sioc.ac.cn.

Abstract

Catalytic cascade transformations of simple starting materials into highly functionalized molecules bearing a stereochemically defined multisubstituted alkene, which are important in medicinal chemistry, natural product synthesis, and material science, are in high demand for organic synthesis. The development of multiple reaction pathways accurately controlled by catalysts derived from different ligands is a critical goal in the field of catalysis. Here we report a cobalt-catalyzed strategy for the direct coupling of inexpensive 1,3-enynes with two molecules of acrylates to construct a high diversity of functionalized 1,3-dienes containing a trisubstituted or tetrasubstituted olefin. Such cascade reactions can proceed through three different pathways initiated by oxidative cyclization to achieve multiple bond formation in high chemo-, regio- and stereoselectivity precisely controlled by ligands, providing a platform for the development of tandem carbon-carbon bond-forming reactions.

Abstract

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