A One-Pot Umpolung Method for Preparation of α-Aryl Nitriles from α-Chloro Aldoximes via Organocuprate Additions to Transient Nitrosoalkenes

Ritobroto Sengupta; Steven M. Weinreb

doi:10.1055/s-0032-1316984

Synthesis, Table of Contents

Synthesis 2012; 44(18): 2933-2937
DOI: 10.1055/s-0032-1316984

paper

A One-Pot Umpolung Method for Preparation of α-Aryl Nitriles from α-Chloro Aldoximes via Organocuprate Additions to Transient Nitrosoalkenes

Ritobroto Sengupta

Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA, Fax: +1(814)8638403 Email: smw@chem.psu.edu

,

Steven M. Weinreb*

Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA, Fax: +1(814)8638403 Email: smw@chem.psu.edu

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Abstract

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Abstract

Conjugate addition of a variety of aryl lithiocyanocuprates to nitrosoalkenes generated from α-chloro aldoximes, followed by in situ dehydration of the crude α-aryl aldoxime product with N,N′-dicyclohexylcarbodiimide, affords α-aryl nitriles in good overall yields via a one-pot protocol.

Key words

cuprates - nucleophilic addition - nitriles - aldehydes - arylation

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References

References
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