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

ABSTRACT: 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.

SUBMITTER: Li MY

PROVIDER: S-EPMC7082552 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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

Li Meng-Yao MY Han Pengbo P Hu Tian-Jiao TJ Wei Dong D Zhang Ge G Qin Anjun A Feng Chen-Guo CG Tang Ben Zhong BZ Lin Guo-Qiang GQ

iScience 20200307 3

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 t ...[more]

PMID: 32199292

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