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

Summary: 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 ena...

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Bibliographic Details
Main Authors: Meng-Yao Li, Pengbo Han, Tian-Jiao Hu, Dong Wei, Ge Zhang, Anjun Qin, Chen-Guo Feng, Ben Zhong Tang, Guo-Qiang Lin
Format: Article
Language:English
Published: Elsevier 2020-03-01
Series:iScience
Online Access:http://www.sciencedirect.com/science/article/pii/S2589004220301504
Description
Summary:Summary: 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. : Molecular Interactions with Photons; Organic Chemistry; Physical Organic Chemistry Subject Areas: Molecular Interactions with Photons, Organic Chemistry, Physical Organic Chemistry
ISSN:2589-0042