A catalyst-free strategy for regioselective hydroxydifluoroalkylation of alkenes with alkyl bromides was developed, affording a series of difluoroalkylated tertiary alcohols in moderate to good yields. This photocatalyst-free protocol shows broad substrate scope under mild conditions. Moreover, mechanistic studies revealed that a newly identified electron donor−acceptor complex is crucial to this transformation.
Reported
herein is a photoredox-catalyzed amination of o-hydroxyarylenaminones
with tert-butyl
((perfluoropyridin-4-yl)oxy) carbamate, a versatile amidyl-radical
precursor developed in our laboratory. This work establishes a new
cascade pathway for the assembly of a range of 3-aminochromones under
mild conditions. Downstream transformations of the obtained 3-aminochromones
to construct diverse amino pyrimidines greatly broaden the applications
of this photocatalyzed protocol.
An unprecedented photoredox‐catalyzed phosphine‐mediated deoxygenation of hexafluoroacetone hydrate was established to accomplish the hydroxylpolyfluoroalkylation of electron‐deficient alkenes. A range of bis(trifluoromethyl)carbinols were facilely accessed by using readily available hexafluoroacetone hydrate, instead of toxic gaseous hexafluoroacetone. A range of electron‐deficient alkenes are tolerated, giving the corresponding hydro‐hydroxylpolyfluoroalkylated products in moderate to high yields. Remarkable features of this synthetic strategy include operational simplicity, mild reaction conditions, excellent regioselectivity, and broad functional group tolerance. The success of this strategy relies on the delicate utilization of aldehyde/ketone‐gem‐diol intrinsic equilibrium, which offers an innovated open‐shell pathway for the assembly of synthetically challenging polyfluoroalkylated scaffolds.
A metal-free photosensitized three-component reaction of oxime esters, alkenes, and DABCO•(SO 2 ) 2 was developed. This protocol could accommodate a wide substrate scope, including activated and unactivated alkenes and aryl and aliphatic carboxylic acid oxime esters, delivering a broad range of βamino sulfones in moderate to high yields. The insertion of SO 2 as a linker moiety allows the manipulation of the functionality in the reaction process, expanding the utility of oxime esters as bifunctional reagents.
Background: Identification of novel Ure inhibitors with high potency has received considerable attention. Methodology/results: Ure inhibition was determined using the indophenol method, the affinities to Ure were estimated via surface plasmon resonance. Seventeen new plus ten known N-monosubstituted thiosemicarbazides were synthesized and identified as novel Ure inhibitors. Out of these compounds, compound b5 shows excellent activity against both crude Ure from Helicobacter pylori (IC50 = 0.04 μM) and Ure in living cell (IC50 = 0.27 μM), with the potency being over 600-fold higher than clinical used drug acetohyroxamic acid, respectively. Surface plasmon resonance demonstrated the high affinity ( Kd.#x00A0;= 6.32 nM) of b5 to Ure. Conclusion: This work provides a class of novel and promising Ure inhibitors.
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