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Regiospecific decarboxylative allylation of nitriles
Recio, Antonio, III Tunge, Jon A.
Recio, Antonio, III
Tunge, Jon A.
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Abstract
Palladium-catalyzed decarboxylative α-allylation of nitriles readily occurs using Pd2(dba)3 and rac-BINAP. This catalyst mixture also allows the highly regiospecific α-allylation of nitriles in the presence of much more acidic α-protons. Thus, the reported method provides access to compounds that are not readily available via base-mediated allylation chemistries. Lastly, mechanistic investigations indicate that there is a competition between C- and N-allylation of an intermediate nitrile-stabilized anion and that N-allylation is followed by a rapid [3,3]-sigmatropic rearrangement.
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2009-12-17
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American Chemical Society
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Recio, A., & Tunge, J. A. (2009). Regiospecific decarboxylative allylation of nitriles. Organic Letters, 11(24), 5630–5633. http://doi.org/10.1021/ol902065p