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Synlett 2013; 24(5): 619-624
DOI: 10.1055/s-0032-1318237
DOI: 10.1055/s-0032-1318237
letter
Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides
Further Information
Publication History
Received: 27 December 2012
Accepted after revision: 28 January 2013
Publication Date:
20 February 2013 (online)
Abstract
This work highlights unsymmetrical biaryl compounds via direct nickel-catalyzed reductive coupling of two aryl halides. By tuning the ligand structures, the reaction of two electron-enriched aryl halides also provided the coupling product in good yields, with an excess of 1.4 equivalents of one of the halides. The mild reaction conditions display excellent functional-group tolerance and generally gave the coupling products in moderate to good yields. In addition to aryl bromides, activated aryl chlorides are effective.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References
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For C-H activation, see:
For selected examples of C(sp3)–C(sp2) coupling without in situ organometallic reagents, see:
With in situ organometallic formation:
For catalytic C(sp3)–C(sp3) coupling, see:
For mechanistic discussions on the Ni-catalyzed reductive coupling of aryl–aryl halides involving NiI and NiIII intermediates, see: