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Design of a mesoscale continuous-flow route toward lithiated methoxyallene

Sofie Seghers (UGent) , Thomas Heugebaert (UGent) , Matthias Moens (UGent) , Jolien Sonck, Joris Thybaut (UGent) and Christian Stevens (UGent)
(2018) CHEMSUSCHEM. 11(13). p.2248-2254
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Abstract
The unique nucleophilic properties of lithiated methoxyallene allow for C-C bond formation with a wide variety of electrophiles, thus introducing an allenic group for further functionalization. This approach has yielded a tremendously broad range of (hetero)cyclic scaffolds, including precursors to active pharmaceutical ingredients. To date, however, its valorization at scale is hampered by the batch synthesis procedure, which suffers from serious safety issues. Hence, the attractive heat- and mass-transfer properties of flow technology were exploited to establish a mesoscale continuous-flow route toward lithiated methoxyallene. An excellent conversion of 94% was obtained, corresponding to a methoxyallene throughput of 8.2gh(-1). The process is characterized by short reaction times, mild reaction conditions and a stoichiometric use of reagents.
Keywords
allenes, flow chemistry, green chemistry, microreactors, BUILDING-BLOCKS, 3-COMPONENT SYNTHESIS, PYRROLE DERIVATIVES, ALLENYL ETHERS, ALKOXYALLENES, 5-ACETYLOXAZOLES, AROMATIZATION, 1, 2-OXAZINES, HETEROCYCLES, HYDRAZONES

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Chicago
Seghers, Sofie, Thomas Heugebaert, Matthias Moens, Jolien Sonck, Joris Thybaut, and Christian Stevens. 2018. “Design of a Mesoscale Continuous-flow Route Toward Lithiated Methoxyallene.” Chemsuschem 11 (13): 2248–2254.
APA
Seghers, Sofie, Heugebaert, T., Moens, M., Sonck, J., Thybaut, J., & Stevens, C. (2018). Design of a mesoscale continuous-flow route toward lithiated methoxyallene. CHEMSUSCHEM, 11(13), 2248–2254.
Vancouver
1.
Seghers S, Heugebaert T, Moens M, Sonck J, Thybaut J, Stevens C. Design of a mesoscale continuous-flow route toward lithiated methoxyallene. CHEMSUSCHEM. 2018;11(13):2248–54.
MLA
Seghers, Sofie, Thomas Heugebaert, Matthias Moens, et al. “Design of a Mesoscale Continuous-flow Route Toward Lithiated Methoxyallene.” CHEMSUSCHEM 11.13 (2018): 2248–2254. Print.
@article{8573436,
  abstract     = {The unique nucleophilic properties of lithiated methoxyallene allow for C-C bond formation with a wide variety of electrophiles, thus introducing an allenic group for further functionalization. This approach has yielded a tremendously broad range of (hetero)cyclic scaffolds, including precursors to active pharmaceutical ingredients. To date, however, its valorization at scale is hampered by the batch synthesis procedure, which suffers from serious safety issues. Hence, the attractive heat- and mass-transfer properties of flow technology were exploited to establish a mesoscale continuous-flow route toward lithiated methoxyallene. An excellent conversion of 94\% was obtained, corresponding to a methoxyallene throughput of 8.2gh(-1). The process is characterized by short reaction times, mild reaction conditions and a stoichiometric use of reagents.},
  author       = {Seghers, Sofie and Heugebaert, Thomas and Moens, Matthias and Sonck, Jolien and Thybaut, Joris and Stevens, Christian},
  issn         = {1864-5631},
  journal      = {CHEMSUSCHEM},
  keyword      = {allenes,flow chemistry,green chemistry,microreactors,BUILDING-BLOCKS,3-COMPONENT SYNTHESIS,PYRROLE DERIVATIVES,ALLENYL ETHERS,ALKOXYALLENES,5-ACETYLOXAZOLES,AROMATIZATION,1,2-OXAZINES,HETEROCYCLES,HYDRAZONES},
  language     = {eng},
  number       = {13},
  pages        = {2248--2254},
  title        = {Design of a mesoscale continuous-flow route toward lithiated methoxyallene},
  url          = {http://dx.doi.org/10.1002/cssc.201800760},
  volume       = {11},
  year         = {2018},
}

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