Computational study on the iodobenzene-catalyzed oxidative cyclization of a δ-alkynyl β-ketoester

Butt, Smaher E.; Rodríguez, Arantxa; Sotiropoulos, Jean-Marc; Moran, Wesley J.

Abstract

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 considered for this process, and of the three, activation of the alkyne by a hypervalent iodine species followed by cyclization was found to be the most likely pathway based upon our computational results.

Citation

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

• Journal Article Type: Article
• Acceptance Date: Apr 1, 2022
• Online Publication Date: Jun 12, 2022
• Deposit Date: Feb 20, 2024
• Publicly Available Date: Feb 29, 2024
• Journal: Arkivoc
• Print ISSN: 1551-7012
• Publisher: Michigan Publishing
• Peer Reviewed: Peer Reviewed
• Volume: 2022
• Issue: 7
• Pages: 19-26
• DOI: https://doi.org/10.24820/ark.5550190.p011.745
• Keywords: Organic Chemistry