19980-01-9Relevant academic research and scientific papers
Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate
Lee, Melissa,Sanford, Melanie S.
, p. 572 - 575 (2017)
This letter describes the development of a method for selective remote C(sp3)-H oxygenation of protonated aliphatic amines using aqueous potassium persulfate. Protonation serves to deactivate the proximal C(sp3)-H bonds of the amine substrates and also renders the amines soluble in the aqueous medium. These reactions proceed under relatively mild conditions (within 2 h at 80 °C with amine as limiting reagent) and do not require a transition metal catalyst. This method is applicable to a variety of types of C(sp3)-H bonds, including 3°, 2°, and benzylic C-H sites in primary, secondary, and tertiary amine substrates.
Biohydroxylation reactions catalyzed by enzymes and whole-cell systems
Flitsch, Sabine L.,Aitken, Suzanne J.,Chow, Cathy S.-Y.,Grogan, Gideon,Staines, Adam
, p. 81 - 90 (2007/10/03)
The biohydroxylation of a number of cyclic substrates (3-24) containing aromatic side chains was used to compare substrate specificity and selectivity of hydroxylation using microbial enzymes and whole-cell biocatalysts. In general, the regioselectivity of reaction was remarkably similar between the different catalysts in that little aromatic or benzylic, but significant aliphatic hydroxylation was observed. However, a more detailed investigation of isolated products showed complementary substrate specificity, functional group compatibility, and regioselectivity of hydroxylation. Substrate specificity and regioselectivity could be further modulated by small changes to the nature of the aromatic side chain, which appears to play an important role in substrate recognition.
