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

Meng-Yao Li; Pengbo Han; Tian-Jiao Hu; Dong Wei; Ge Zhang; Anjun Qin; Chen-Guo Feng; Ben Zhong Tang; Guo-Qiang Lin

iScience (Mar 2020)

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

Meng-Yao Li,
Pengbo Han,
Tian-Jiao Hu,
Dong Wei,
Ge Zhang,
Anjun Qin,
Chen-Guo Feng,
Ben Zhong Tang,
Guo-Qiang Lin

Affiliations

Meng-Yao Li: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China
Pengbo Han: State Key Laboratory of Luminescent Materials and Devices, Key Laboratory of Luminescence from Molecular Aggregates of Guangdong Province, Center for Aggregation-Induced Emission, South China University of Technology, Guangzhou 510640, China
Tian-Jiao Hu: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China
Dong Wei: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China
Ge Zhang: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China
Anjun Qin: State Key Laboratory of Luminescent Materials and Devices, Key Laboratory of Luminescence from Molecular Aggregates of Guangdong Province, Center for Aggregation-Induced Emission, South China University of Technology, Guangzhou 510640, China
Chen-Guo Feng: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China; The Research Center of Chiral Drugs, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China; Corresponding author
Ben Zhong Tang: State Key Laboratory of Luminescent Materials and Devices, Key Laboratory of Luminescence from Molecular Aggregates of Guangdong Province, Center for Aggregation-Induced Emission, South China University of Technology, Guangzhou 510640, China
Guo-Qiang Lin: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China; The Research Center of Chiral Drugs, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China; Corresponding author

Journal volume & issue: Vol. 23, no. 3

Abstract

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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

Published in iScience

ISSN: 2589-0042 (Online)
Publisher: Elsevier
Country of publisher: United States
LCC subjects: Science
Website: http://www.cell.com/iscience/home

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