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Highly Efficient Ruthenium-Catalyzed Oxime to Amide Rearrangement

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Nathan A. Owston,^† Alexandra J. Parker,^‡ and Jonathan M. J. Williams*^†

Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UK, and Process Research and Development, AstraZeneca, Avlon Works, Severn Road, Hallen, Bristol BS10 7ZE, UK

Org. Lett., 2007, 9 (18), pp 3599–3601

DOI: 10.1021/ol701445n

Publication Date (Web): August 8, 2007

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

A wide range of aldoximes has been converted into the corresponding amides using the ruthenium-based catalyst Ru(PPh₃)₃(CO)H₂/dppe/TsOH. The amides are generated in high yield and selectivity, with catalyst loading as low as 0.04 mol %.

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This article has been cited by 7 ACS Journal articles (5 most recent appear below).

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Au/Ag-Cocatalyzed Aldoximes to Amides Rearrangement under Solvent- and Acid-Free Conditions
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Terpyridine Ruthenium-Catalyzed One-Pot Conversion of Aldehydes into Amides
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  TerpyRu(PPh3)Cl2 is an efficient catalyst for rearranging aldoximes to amides without the need for chelating phosphines or additives as in prior examples. The catalyst is also useful in converting aldehydes into amides in a one-pot process using NaHCO3 as ...
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