Suzuki-Miyaura Coupling Enabled by Aryl to Vinyl 1,4-Palladium Migration

• Published in: iScience Vol. 23; no. 3; p. 100966
• Main Authors: Li, Meng-Yao, Han, Pengbo, Hu, Tian-Jiao, Wei, Dong, Zhang, Ge, Qin, Anjun, Feng, Chen-Guo, Tang, Ben Zhong, Lin, Guo-Qiang
• Format: Journal Article
• Language: English
• Published: United States Elsevier Inc 27.03.2020; Elsevier
• Subjects: Molecular Interactions with Photons; Organic Chemistry; Physical Organic Chemistry; Molecular Interactions with Photons; Physical Organic Chemistry; Organic Chemistry
• ISSN: 2589-0042; 2589-0042
• DOI: 10.1016/j.isci.2020.100966

The Suzuki-Miyaura coupling is a fundamentally important transformation in modern organic synthesis. The development of new reaction modes for new chemical accessibility and higher synthetic efficiency is still the consistent pursuance in this field. An efficient Suzuki-Miyaura coupling enabled by a controllable 1,4-palladium migration was realized to afford stereodefined multisubstituted olefins and 1,3-dienes. The reaction exhibits remarkable broad substrate scope, excellent functional-group tolerance, versatile conversion with obtained products, and easy scalability. The practicality of this method is highlighted by the aggregation-induced emission feature of the produced olefins and 1,3-dienes, as well as the capability of affording geometric isomer pairs with a marked difference on photoluminescent quantum yield values. [Display omitted] •Suzuki-Miyaura coupling via controllable aryl to vinyl 1,4-palladium migration•Synthesis of multisubstituted olefins and 1,3-dienes in stereo-specific way•Wide substrate scope and excellent functional-group tolerance•A powerful tool for the studies on geometric isomers in material science Molecular Interactions with Photons; Organic Chemistry; Physical Organic Chemistry