RESUMEN
2,5-Disubstituted furans are frequently found in pharmaceuticals and bioactive natural products. Nucleophilic substitution reactions on the carbon atom adjacent to the furan ring are useful for producing various furan derivatives. However, the formation of 5-substituted 2-halomethylfuran and the subsequent nucleophilic substitution reactions are often limited by severe undesired reactions caused by the highly reactive halomethylfurans. This paper reports the successful rapid synthesis of various 2,5-disubstituted furans using microflow technology, which suppresses undesired reactions including dimerization and ring opening of the furans. We observed that Brønsted acids had a significant effect on the nucleophilic substitution reaction and the use of HBr and HI gave the best results. A plausible mechanism of the Brønsted acid-mediated nucleophilic substitutions in the developed approach was proposed.
RESUMEN
Correction for 'Micro-flow heteroatom alkylation via TfOH-mediated rapid in situ generation of carbocations and subsequent nucleophile addition' by Yuma Matsuura et al., Chem. Commun., 2024, https://doi.org/10.1039/D3CC06308A.
RESUMEN
A rapid nucleophilic substitution reaction was developed using carbocations generated from diarylmethanol and trifluoromethanesulfonic acid. Undesired reactions caused by the carbocations were suppressed, presumably due to the rapid and uniform generation of carbocations and the subsequent rapid and uniform distribution of nucleophiles by the micro-flow technology.
