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ChemComm
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DOI: 10.1039/D0CC01533D
COMMUNICATION
9
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Additionally, simple RuCl3 could be used as the metal source for
the direct vinylation of 5-methyloxazolidinone 2b affording full
conversion to the product 3b (see ESI, S6). After a brief
optimization of the reaction conditions it was found that the
best result is achieved by using 6 mol% of RuCl3 hydrate and
12% of P(nBu)3 in toluene at 100 °C. Notably, the addition of
DMAP led to a decrease of the conversion of product 3b while
the use of PPh3 afforded zero product formation (see ESI, S6).
RuCl3 would give an economical advantage due to the
inexpensiveness of the ruthenium source.
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Conclusion
In conclusion, here we reported for the first time the use of
acetylene under low pressure for one step vinylation of
different cyclic N-nucleophiles, affording a broad scope of N-
vinyl amides of high industrial interest. Additionally, the
reported catalytic system has a great advantage for preparative
application due to its suitability for an expanded range of N-
nucleophiles, which are often not compatible with the harsh
reaction conditions of standard Reppe chemistry. Among the
synthesis of the commercially important N-vinylated
compounds (3a, 3b, 3c), a number of new substrates with
potential application as a versatile synthetic building blocks
were prepared (3d, 3e, 3f, 3g, 3h, 3i, 3l, 3m, 3n, 3o, 3p, 3r, 3u).
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Conflicts of interest
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A patent application from the same authors on this topic was also
filed (EP 19218545.2)
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Acknowledgment
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CaRLa (Catalysis Research Laboratory) is cofinanced by the Ruprecht-
Karls-Universität Heidelberg (Heidelberg University) and BASF SE.
Notes and references
1
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