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Hypervalent iodine mediated cyclization of bishomoallylamides to prolinols (2024)
Working Paper
Butt, S. E., Kepski, K., Sotiropoulos, J., & Moran, W. J. Hypervalent iodine mediated cyclization of bishomoallylamides to prolinols

A change in mechanism was observed in the hypervalent iodine mediated cyclization of N-alkenylamides when the carbon chain between the alkene and the amide increased from two to three atoms. In the latter case, cyclization at the amide nitrogen to fo... Read More about Hypervalent iodine mediated cyclization of bishomoallylamides to prolinols.

Toward a General Protocol for Catalytic Oxidative Transformations Using Electrochemically Generated Hypervalent Iodine Species (2023)
Journal Article
Elsherbini, M., & Moran, W. J. (2023). Toward a General Protocol for Catalytic Oxidative Transformations Using Electrochemically Generated Hypervalent Iodine Species. Journal of Organic Chemistry, 88(3), 1424-1433. https://doi.org/10.1021/acs.joc.2c02309

A simple catalytic electrosynthetic protocol for oxidative transformations mediated by hypervalent iodine reagents has been developed. In this protocol, electricity drives the iodine(I)/iodine(III) catalytic cycle enabling catalysis with in situ gene... Read More about Toward a General Protocol for Catalytic Oxidative Transformations Using Electrochemically Generated Hypervalent Iodine Species.

An Unexpected Reaction between Diaryliodonium Salts and DMSO (2022)
Journal Article
Kepski, K., & Moran, W. J. (2022). An Unexpected Reaction between Diaryliodonium Salts and DMSO. Organics, 3(3), 275-280. https://doi.org/10.3390/org3030020

Diaryliodonium salts are useful arylating reagents that have been exploited widely. In this Communication, we demonstrate that heating diphenyliodonium triflate in the solvent DMSO leads to an unexpected arylation reaction. It is postulated that aryl... Read More about An Unexpected Reaction between Diaryliodonium Salts and DMSO.

Computational study on the iodobenzene-catalyzed oxidative cyclization of a δ-alkynyl β-ketoester (2022)
Journal Article
Butt, S. E., Rodríguez, A., Sotiropoulos, J., & Moran, W. J. (in press). Computational study on the iodobenzene-catalyzed oxidative cyclization of a δ-alkynyl β-ketoester. Arkivoc, 2022(7), 19-26. https://doi.org/10.24820/ark.5550190.p011.745

The iodobenzene-catalyzed oxidative cyclization of a δ-alkynyl β-ketoester has been investigated by density functional theory (DFT) calculations at the CPCM(acetonitrile)/B3LYP/6-311++G(d,p)//B3LYP/SDD(I) levels. Three different mechanisms were consi... Read More about Computational study on the iodobenzene-catalyzed oxidative cyclization of a δ-alkynyl β-ketoester.

Scalable electrochemical synthesis of diaryliodonium salts (2021)
Journal Article
Elsherbini, M., & Moran, W. J. (2021). Scalable electrochemical synthesis of diaryliodonium salts. Organic and Biomolecular Chemistry, 19(21), 4706-4711. https://doi.org/10.1039/d1ob00457c

Cyclic and acyclic diaryliodonium are synthesised by anodic oxidation of iodobiaryls and iodoarene/arene mixtures, respectively, in a simple undivided electrolysis cell in MeCN–HFIP–TfOH without any added electrolyte salts. This atom efficient proces... Read More about Scalable electrochemical synthesis of diaryliodonium salts.

Synthesis of Oxazolidinones by a Hypervalent Iodine Mediated Cyclization of N‐Allylcarbamates (2021)
Journal Article
Das, M., Rodríguez, A., Lo, P. K. T., & Moran, W. J. (2021). Synthesis of Oxazolidinones by a Hypervalent Iodine Mediated Cyclization of N‐Allylcarbamates. Advanced synthesis & catalysis, 363(6), 1646-1650. https://doi.org/10.1002/adsc.202001451

The preparation of oxazolidinones by the hypervalent iodine mediated cyclization of allylcarbamates is described. A versatile range of substrates can be converted into substituted oxazolidinones primed for further transformations. Derivatization of t... Read More about Synthesis of Oxazolidinones by a Hypervalent Iodine Mediated Cyclization of N‐Allylcarbamates.

Spirooxazoline Synthesis by an Oxidative Dearomatizing Cyclization (2020)
Journal Article
Tariq, M. U., & Moran, W. J. (2020). Spirooxazoline Synthesis by an Oxidative Dearomatizing Cyclization. European Journal of Organic Chemistry, 2020(32), 5153-5160. https://doi.org/10.1002/ejoc.202000840

Spirocyclic compounds are of increasing importance owing to their potential applications in the development of new pharmaceuticals. Herein, we describe a new, rapid access to rarely seen spirooxazolines utilizing an I(I)/I(III) reaction manifold. The... Read More about Spirooxazoline Synthesis by an Oxidative Dearomatizing Cyclization.

Computationally Assisted Mechanistic Investigation into Hypervalent Iodine Catalysis: Cyclization of N-Allylbenzamide (2019)
Journal Article
Butt, S., Das, M., Sotiropoulos, J., & Moran, W. (2019). Computationally Assisted Mechanistic Investigation into Hypervalent Iodine Catalysis: Cyclization of N-Allylbenzamide. Journal of Organic Chemistry, 84(23), 15605–15613. https://doi.org/10.1021/acs.joc.9b02623

Previous experimental work identified 2-iodoanisole as the best precatalyst for the oxidative cyclization of N-alkenylamides into 2-oxazolines. Herein, we describe our investigation into the effect on the reaction rate based on the structure of the i... Read More about Computationally Assisted Mechanistic Investigation into Hypervalent Iodine Catalysis: Cyclization of N-Allylbenzamide.

Iodoarene-catalyzed cyclizations of N-propargylamides and β-amidoketones: synthesis of 2-oxazolines (2017)
Journal Article
Kamouka, S., & Moran, W. J. (2017). Iodoarene-catalyzed cyclizations of N-propargylamides and β-amidoketones: synthesis of 2-oxazolines. Beilstein Journal of Organic Chemistry, 13, 1823–1827. https://doi.org/10.3762/bjoc.13.177

Two complementary iodoarene-catalyzed methods for the preparation of 2-oxazolines are presented. The first involves the cyclization of N-propargylamides and the second involves the cyclization of β-amidoketones. These are proposed to proceed through... Read More about Iodoarene-catalyzed cyclizations of N-propargylamides and β-amidoketones: synthesis of 2-oxazolines.

Preparation and Synthetic Utility of Stable 1,3-Enynyl- and 1,3-Dienyl(aryl)iodonium Salts (2017)
Journal Article
Zawia, E., Hamnett, D. J., & Moran, W. J. (2017). Preparation and Synthetic Utility of Stable 1,3-Enynyl- and 1,3-Dienyl(aryl)iodonium Salts. Journal of Organic Chemistry, 82(7), 3960–3964. https://doi.org/10.1021/acs.joc.7b00192

The facile synthesis of stable enynyl- and dienyl(aryl)iodonium salts is achieved from terminal enynes. An X-ray crystal structure of an example of the latter is presented. These compounds are shown to be useful in a range of transformations.

Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides (2016)
Journal Article
Zawia, E., & Moran, W. (2016). Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides. Molecules, 21(8), Article 1073. https://doi.org/10.3390/molecules21081073

Vinyl(aryl)iodonium salts are useful compounds in organic synthesis but they are under-utilized and their chemistry is under-developed. Herein is described the solvolysis of some vinyl(phenyl)iodonium salts, bearing an arylsulfonyl group, in aqueous... Read More about Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides.

Studies on the Pd-catalyzed dimerization of silacyclobutanes (2015)
Journal Article
Aborways, M., & Moran, W. (2015). Studies on the Pd-catalyzed dimerization of silacyclobutanes. Journal of Organometallic Chemistry, 797, 57-59. https://doi.org/10.1016/j.jorganchem.2015.07.040

Dimerization of silacyclobutanes has been achieved under palladium catalysis at room temperature. A previous report described the requirement for high temperature and a stoichiometric amount of palladium complex to effect this process.

Iodoarene-catalyzed cyclizations of unsaturated amides (2015)
Journal Article
Moran, W., Alhalib, A., & Kamouka, S. (2015). Iodoarene-catalyzed cyclizations of unsaturated amides. Organic Letters, https://doi.org/10.1021/acs.orglett.5b00333

The cyclization of N-alkenylamides catalyzed by iodoarenes under oxidative conditions is presented. Five-, six-, and seven-membered rings with a range of substitutions can be prepared by this route. Preliminary data from the use of chiral iodoarenes... Read More about Iodoarene-catalyzed cyclizations of unsaturated amides.

Improving alkynyl(aryl)iodonium salts: 2-anisyl as a superior aryl group (2014)
Journal Article
Moran, W., & Hamnett, D. (2014). Improving alkynyl(aryl)iodonium salts: 2-anisyl as a superior aryl group. Organic and Biomolecular Chemistry, 12(24), https://doi.org/10.1039/c4ob00556b

The majority of alkynyl(aryl)iodonium salts reported in the literature are derived from iodobenzene. This article describes the effects of varying this iodoarene building block on the synthesis, reactivity and stability of these salts. Two procedures... Read More about Improving alkynyl(aryl)iodonium salts: 2-anisyl as a superior aryl group.

Reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions (2014)
Journal Article
Aborways, M. M., & Moran, W. J. (2014). Reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions. Tetrahedron Letters, 55(13), 2127-2129. https://doi.org/10.1016/j.tetlet.2014.02.042

The study of the reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions is presented. With sodium iodide, α-iodoenones were formed, however, with sodium bromide or chloride the α-haloenones were only formed in low yie... Read More about Reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions.

CuI-catalyzed cycloisomerization of propargyl amides (2013)
Journal Article
Moran, W., & Alhalib, A. (2014). CuI-catalyzed cycloisomerization of propargyl amides. Organic and Biomolecular Chemistry, 12(5), 795-800. https://doi.org/10.1039/c3ob42030b

The synthesis of substituted dihydrooxazoles by the CuI-catalyzed cycloisomerization of terminal propargyl amides is reported. The reaction has been shown to have good substrate scope and experiments to delineate the mechanism have been performed. Su... Read More about CuI-catalyzed cycloisomerization of propargyl amides.

Oxidative rearrangement of tertiary propargylic alcohols (2012)
Journal Article
Rodríguez, A., & Moran, W. J. (2013). Oxidative rearrangement of tertiary propargylic alcohols. SYNLETT, 24(1), 102-104. https://doi.org/10.1055/s-0032-1317711

An oxidative rearrangement of tertiary alcohols mediated by m-CPBA is described that generates tetrasubstituted alkenes with a carboxylic acid substituent. The mechanism of the reaction is proposed to proceed through epoxidation of the alkyne to form... Read More about Oxidative rearrangement of tertiary propargylic alcohols.