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Synfacts 2014; 10(5): 0515
DOI: 10.1055/s-0033-1341218
DOI: 10.1055/s-0033-1341218
Metal-Mediated Synthesis
Stereospecific Kumada Cross-Coupling of Alkyl and Aryl Grignards
Yonova IM, Johnson AG, Osborne CA, Moore CE, Morrissette NS, Jarvo ER * University of California, Irvine and University of California, San Diego, USA
Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Grignard Reagents and Identification of Selective Anti-Breast-Cancer Agents.
Angew. Chem. Int. Ed. 2014;
53: 2422-2427
Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Grignard Reagents and Identification of Selective Anti-Breast-Cancer Agents.
Angew. Chem. Int. Ed. 2014;
53: 2422-2427
Further Information
Publication History
Publication Date:
17 April 2014 (online)
Significance
Herein, the authors report an efficient nickel-catalyzed cross-coupling reaction of long-chain alkyl and various aryl Grignards with benzylic ethers providing the corresponding products with high enantiospecificity. Furthermore, applying this reaction protocol, compounds that show promising inhibition of breast cancer cell proliferation could be prepared.
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Comment
Decreasing the reaction concentration raised the efficiency of the transformation and less elimination byproduct was generated. Also, the use of more than two equivalents of Grignard reagent was disadvantageous for the reaction.
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