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Synfacts 2014; 10(3): 0307
DOI: 10.1055/s-0033-1340756
DOI: 10.1055/s-0033-1340756
Metal-Mediated Synthesis
Coupling of Arylzinc Reagents with Aryl and Alkenyl Halides
Shirakawa E, * Tamakuni F, Kusano E, Uchiyama N, Konagaya W, Watabe R, Hayashi T. Kyoto University, Japan; Institute of Materials Research and Engineering, Singapore
and National University of Singapore, Singapore
Single-Electron-Transfer-Induced Coupling of Arylzinc Reagents with Aryl and Alkenyl Halides.
Angew. Chem. Int. Ed. 2014;
53: 521-525
Single-Electron-Transfer-Induced Coupling of Arylzinc Reagents with Aryl and Alkenyl Halides.
Angew. Chem. Int. Ed. 2014;
53: 521-525
Further Information
Publication History
Publication Date:
17 February 2014 (online)
Significance
Single-electron transfer (SET) from arylzinc reagents to aryl and alkenyl halides makes cross-coupling possible without the need for transition metals. Compared to an already reported procedure by the same group using Grignard reagents (Angew. Chem. Int. Ed. 2012, 51, 218), the new protocol tolerates a wider range of functional groups.
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Comment
Interestingly, lithium chloride considerably enhances the reactivity of the arylzinc reagents, ensuring short reaction times. Reactions of phenylzinc iodide and (E)- or (Z)-1-octenyl iodide furnish the corresponding coupling products with retention of stereochemistry, ruling out the presence of a σ-radical species.
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