Outputs (19)

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.