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Synfacts 2012; 8(6): 0655
DOI: 10.1055/s-0031-1291110
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Negishi Cross-Coupling Using Aryl Ethers as Coupling Partners

Contributor(s):
Paul Knochel
,
Nadja M. Barl
Wang C, * Ozaki T, Takita R, Uchiyama M. * RIKEN, Advanced Science Institute, Saitama and The University of Tokyo, Japan
Aryl Ether as a Negishi Coupling Partner: An Approach for Constructing C–C Bonds under Mild Conditions.

Chem. Eur. J. 2012;
18: 3482-3485
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Further Information

Publication History

Publication Date:
16 May 2012 (online)

 
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Key words

zinc - nickel - aryl ethers - C–O activation - cross-coupling

Significance

The first nickel-catalyzed cross-­coupling of aryl ethers with aromatic zincates via C–O bond cleavage is described. The corresponding biaryls are obtained in moderate to good yields. Electron-rich coupling partners furnish higher product yields than reagents containing electron-withdrawing groups.


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Comment

It is noteworthy that, besides the methoxy moiety, this methodology may be extended to ethyl and isopropyl ethers as well. Furthermore, this protocol allows a facile conversion of chiral substrates into the corresponding biaryls without racemization.


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