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Continuous flow synthesis of sulfur‐ and selenium−NHC compounds (NHC=N‐heterocyclic carbene)

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Abstract
The first continuous flow syntheses of sulfur- and selenium-NHC (NHC=N-heterocyclic carbene) adducts in unprecedented short reaction times and high yields are reported. The importance of these species in coordination chemistry or as efficient tools for determining the pi-acceptor character of NHC ligands make any improvement in their synthesis a worthy goal. Thiourea derivatives bearing both saturated and unsaturated NHCs were obtained using NEt3 as a weak base (homogeneous setup) in conjunction with a bed of elemental sulfur (S-8). The synthetic route proving optimal for selenoureas involves the use of a simple Se/K2CO3 heterogeneous microreactor design.
Keywords
Organic Chemistry, Physical and Theoretical Chemistry, Carbenes, Continuous flow synthesis, Sustainable chemistry, Thioureas and selenoureas, Weak base route, CHEMICAL-SHIFTS, COMPLEXES

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Citation

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MLA
Cauwenbergh, Thibault, et al. “Continuous Flow Synthesis of Sulfur‐ and Selenium−NHC Compounds (NHC=N‐heterocyclic Carbene).” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2022, no. 15, 2022, doi:10.1002/ejoc.202101296.
APA
Cauwenbergh, T., Scattolin, T., Simoens, A., Tzouras, N., Stevens, C., & Nolan, S. (2022). Continuous flow synthesis of sulfur‐ and selenium−NHC compounds (NHC=N‐heterocyclic carbene). EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022(15). https://doi.org/10.1002/ejoc.202101296
Chicago author-date
Cauwenbergh, Thibault, Thomas Scattolin, Andreas Simoens, Nikolaos Tzouras, Christian Stevens, and Steven Nolan. 2022. “Continuous Flow Synthesis of Sulfur‐ and Selenium−NHC Compounds (NHC=N‐heterocyclic Carbene).” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2022 (15). https://doi.org/10.1002/ejoc.202101296.
Chicago author-date (all authors)
Cauwenbergh, Thibault, Thomas Scattolin, Andreas Simoens, Nikolaos Tzouras, Christian Stevens, and Steven Nolan. 2022. “Continuous Flow Synthesis of Sulfur‐ and Selenium−NHC Compounds (NHC=N‐heterocyclic Carbene).” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2022 (15). doi:10.1002/ejoc.202101296.
Vancouver
1.
Cauwenbergh T, Scattolin T, Simoens A, Tzouras N, Stevens C, Nolan S. Continuous flow synthesis of sulfur‐ and selenium−NHC compounds (NHC=N‐heterocyclic carbene). EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2022;2022(15).
IEEE
[1]
T. Cauwenbergh, T. Scattolin, A. Simoens, N. Tzouras, C. Stevens, and S. Nolan, “Continuous flow synthesis of sulfur‐ and selenium−NHC compounds (NHC=N‐heterocyclic carbene),” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2022, no. 15, 2022.
@article{8744714,
  abstract     = {{The first continuous flow syntheses of sulfur- and selenium-NHC (NHC=N-heterocyclic carbene) adducts in unprecedented short reaction times and high yields are reported. The importance of these species in coordination chemistry or as efficient tools for determining the pi-acceptor character of NHC ligands make any improvement in their synthesis a worthy goal. Thiourea derivatives bearing both saturated and unsaturated NHCs were obtained using NEt3 as a weak base (homogeneous setup) in conjunction with a bed of elemental sulfur (S-8). The synthetic route proving optimal for selenoureas involves the use of a simple Se/K2CO3 heterogeneous microreactor design.}},
  articleno    = {{e202101296}},
  author       = {{Cauwenbergh, Thibault and Scattolin, Thomas and Simoens, Andreas and Tzouras, Nikolaos and Stevens, Christian and Nolan, Steven}},
  issn         = {{1434-193X}},
  journal      = {{EUROPEAN JOURNAL OF ORGANIC CHEMISTRY}},
  keywords     = {{Organic Chemistry,Physical and Theoretical Chemistry,Carbenes,Continuous flow synthesis,Sustainable chemistry,Thioureas and selenoureas,Weak base route,CHEMICAL-SHIFTS,COMPLEXES}},
  language     = {{eng}},
  number       = {{15}},
  pages        = {{20}},
  title        = {{Continuous flow synthesis of sulfur‐ and selenium−NHC compounds (NHC=N‐heterocyclic carbene)}},
  url          = {{http://doi.org/10.1002/ejoc.202101296}},
  volume       = {{2022}},
  year         = {{2022}},
}

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