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Decarboxylative Pal...
Decarboxylative Palladium(II)-Catalyzed Synthesis of Aryl Amidines from Aryl Carboxylic Acids : Development and Mechanistic Investigation
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- Rydfjord, Jonas (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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- Svensson, Fredrik (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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- Trejos, Alejandro (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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- Sjöberg, Per J. R. (author)
- Uppsala universitet,Analytisk kemi
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- Sköld, Christian (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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- Sävmarker, Jonas (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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- Odell, Luke R. (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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- Larhed, Mats (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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(creator_code:org_t)
- 2013-08-28
- 2013
- English.
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In: Chemistry - A European Journal. - : Wiley. - 0947-6539 .- 1521-3765. ; 19:41, s. 13803-13810
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https://doi.org/10.1...
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Abstract
Subject headings
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- A fast and convenient synthesis of aryl amidines starting from carboxylic acids and cyanamides is reported. The reaction was achieved by palladium(II)-catalysis in a one-step microwave protocol using [Pd(O2CCF3)(2)], 6-methyl-2,2-bipyridyl and trifluoroacetic acid (TFA) in N-methylpyrrolidinone (NMP), providing the corresponding aryl amidines in moderate to excellent yields. The protocol is very robust with regards to the cyanamide coupling partner but requires electron-rich ortho-substituted aryl carboxylic acids. Mechanistic insight was provided by a DFT investigation and direct ESI-MS studies of the reaction. The results of the DFT study correlated well with the experimental findings and, together with the ESI-MS study, support the suggested mechanism. Furthermore, a scale-out (scale-up) was performed with a non-resonant microwave continuous-flow system, achieving a maximum throughput of 11mmolh(-1) by using a glass reactor with an inner diameter of 3mm at a flow rate of 1mLmin(-1).
Keyword
- decarboxylation
- density functional calculations
- mass spectrometry
- microwave chemistry
- palladium
Publication and Content Type
- ref (subject category)
- art (subject category)
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