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Synthesis, Characterization, and Reactivity of Arylpalladium Cyanoalkyl Complexes: Selection of Catalysts for the α-Arylation of Nitriles

Darcy A. Culkin and John F. Hartwig*

*Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, Email:

D. A. Culkin, J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 9330-9331.

DOI: 10.1021/ja026584h (free Supporting Information)

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A palladium-catalyzed α-arylation of nitriles was developed by exploring the structure and reactivity of arylpalladium cyanoalkyl complexes. The high yields and short reaction times observed for BINAP-ligated complexes suggested that BINAP-ligated palladium catalysts might be appropriate for the arylation of nitriles. Initial results on a palladium-catalyzed process for the direct coupling of aryl bromides and primary, benzylic, and secondary nitrile anions to form α-aryl nitriles in good yields are reported.

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Key Words

α-Arylation, Nitriles

ID: J48-Y2002-1230