Hydroamidation of Alkenes with N-Substituted Formamides

Dilip Chandra Deb Nath; Christopher M. Fellows; Toshiaki Kobayashi; Teruyuki Hayashi

doi:10.1071/CH06010

RESEARCH ARTICLE

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Hydroamidation of Alkenes with N-Substituted Formamides

Dilip Chandra Deb Nath ^A ^B , Christopher M. Fellows ^A ^C , Toshiaki Kobayashi ^B and Teruyuki Hayashi ^B

+ Author Affiliations

- Author Affiliations

^A Division of Chemistry, School of Biological, Biomedical, and Molecular Sciences, University of New England, Armadale NSW 2351, Australia.

^B Green Chemistry, Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki 305-8565, Japan.

^C Corresponding author. Email: cfellows@une.edu.au

Australian Journal of Chemistry 59(3) 218-224 https://doi.org/10.1071/CH06010
Submitted: 23 December 2005 Accepted: 15 February 2006 Published: 24 March 2006

Abstract

Hydroamidation of olefins with N-substituted formamides is performed with dodecacarbonyltriruthenium (Ru₃(CO)₁₂) at 180°C under N₂ or CO atmosphere in toluene and in a series of ionic liquids. Yields of 99% with 94–97% exo selectivity are found in the addition of N-methylformamide to 2-norbornene under CO both in toluene and in the ionic liquid 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [bmim][NTf₂]. The presence of CO or a phosphine is necessary for significant reaction to occur, with CO more effective than triphenylphosphine in all ionic liquids investigated. Reasonable yields are achieved at low pressures, in contrast to most reported hydroamidations. Conversion, exo-selectivity, and selectivity fall with increasing steric bulk of the N-formamide substituent, and disubstituted formamides are inactive. Of the terminal alkenes investigated, only styrene can be hydroamidated.

References

Hydroamidation of Alkenes with N-Substituted Formamides

Abstract

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