C3-Alkylation of furfural derivatives by continuous flow homogeneous catalysis

The C3-functionalization of furfural using homogeneous ruthenium catalysts requires the preinstallation of an -directing imine group, as well as high temperatures, which did not allow scaling up, at least under batch conditions. In order to design a safer process, we set out to develop a continuous...

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Bibliographic Details
Published in:	Beilstein journal of organic chemistry Vol. 19; no. 1; pp. 582 - 592
Main Authors:	Kinkutu, Grédy Kiala, Louis, Catherine, Roy, Myriam, Blanchard, Juliette, Oble, Julie
Format:	Journal Article
Language:	English
Published:	Germany Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 2023 Beilstein-Institut
Subjects:	Alkylation Batch processes biomass Catalysis Catalysts Chemical Sciences Chemistry c–h activation flow Full Research Paper Furfural High temperature homogeneous catalysis Ligands Optimization Reproducibility Transposition C–H activation biomass homogeneous catalysis furfural flow C-H activation biomass C-H activation flow furfural homogeneous catalysis
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Summary:	The C3-functionalization of furfural using homogeneous ruthenium catalysts requires the preinstallation of an -directing imine group, as well as high temperatures, which did not allow scaling up, at least under batch conditions. In order to design a safer process, we set out to develop a continuous flow process specifically for the C3-alkylation of furfural (Murai reaction). The transposition of a batch process to a continuous flow process is often costly in terms of time and reagents. Therefore, we chose to proceed in two steps: the reaction conditions were first optimized using a laboratory-built pulsed-flow system to save reagents. The optimized conditions in this pulsed-flow mode were then successfully transferred to a continuous flow reactor. In addition, the versatility of this continuous flow device allowed both steps of the reaction to be carried out, namely the formation of the imine directing group and the C3-functionalization with some vinylsilanes and norbonene.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1860-5397 2195-951X 1860-5397
DOI:	10.3762/bjoc.19.43