Boron trifluoride etherate functioning as a fluorine source in an iodosobenzene-mediated intramolecular aminofluorination of homoallylic amines.

doi:10.1021/ol500238k

Paper

Boron trifluoride etherate functioning as a fluorine source in an iodosobenzene-mediated intramolecular aminofluorination of homoallylic amines.

Published Feb 26, 2014 · Jian Cui, Qun Jia, Ruozhu Feng

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Abstract

A widely used Lewis acid BF3·Et2O was shown to be capable of acting as an efficient fluorinating agent in an intramolecular aminofluorination reaction of homoallylic amines to provide 3-fluoropyrrolidines mediated by a commercially available hypervalent iodine(III) reagent PhIO at room temperature. A mechanism involving a carbocation intermediate was proposed on the basis of several experimental evidence.

Study Snapshot

Boron trifluoride etherate acts as an efficient fluorinating agent in an iodosobenzene-mediated intramolecular aminofluorination of homoallylic amines, providing 3-fluoropyrrolidines at room temperature.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Boron trifluoride etherate functioning as a fluorine source in an iodosobenzene-mediated intramolecular aminofluorination of homoallylic amines.

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References

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Prolyl-fluoropyrrolidine derivatives, particularly compounds 9 and 10, show potent dipeptidyl peptidase IV inhibitory activity, reducing glucose excursion in streptozotocin-induced diabetic rats.

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This metal-free method allows for efficient synthesis of fluorinated molecules by directly converting C(sp3)-H bonds to C(sp3)-F bonds using a catalytic N-oxyl radical and Selectfluor.

Citations

BF3·Et2O-promoted unconventional reactions of 2-oxoaldehyde: access to 4-amidooxazoles and β-keto amides/sulphonamides.

BF3OEt2 catalysis offers a novel, efficient, and simple synthetic route to valuable compounds like 4-amidooxazoles and -keto amides/sulphonamides, highlighting the versatility of boron Lewis acids in organic transformations.

Hypervalent iodine-mediated intramolecular alkene halocyclisation

Hypervalent iodine reagents are effective, inexpensive, and environmentally friendly for the synthesis of halogenated cyclic compounds using carbon, oxygen, nitrogen, or sulfur nucleophiles.

BF3 ⋅ OEt2 as a Versatile Reagent: Applications in Organic Synthesis

BF3 OEt2 is a versatile reagent for various organic transformations, particularly in the synthesis of heterocyclic systems and natural products.

BF3-Promoted Ring Expansion of Iminylphosphiranes and Acylphosphiranes for Divergent Access to 1,2-Azaphospholidines and 1,2-Dihydrophosphetes.

BF3Et2O enables ring expansion of phosphiranes, leading to the synthesis of 1,2-azaphospholidines and 1,2-dihydrophosphetes, with the reaction path tuned by nucleophilicity of N and O atoms.

Pd-catalyzed synthesis of hetero 1,2-interlinked C-disaccharides by coupling of iodo glycals with glycals.

Pd-catalyzed synthesis of C1-C2 interlinked disaccharides is a facile method for obtaining chiral ketones from readily available iodo-glycals and unsubstituted glycals.