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

Smaher Butt; Arantxa Rodriguez; Jean-Marc Sotiropoulos; Wesley Moran

doi:10.24820/ark.5550190.p011.745

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

Smaher Butt, Arantxa Rodriguez, Jean-Marc Sotiropoulos, Wesley Moran

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	19-26
Number of pages	8
Journal	Arkivoc
Volume	2022
Issue number	vii
Early online date	12 Jun 2022
DOIs	https://doi.org/10.24820/ark.5550190.p011.745
Publication status	Published - 12 Jun 2022

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title = "Computational study on the iodobenzene-catalyzed oxidative cyclization of a δ-alkynyl β-ketoester",

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.",

keywords = "DFT calculations, Iodine compounds, Catalysis, Organic Chemistry, Hypervalent iodine, DFT, Alkyne, cyclization",

author = "Smaher Butt and Arantxa Rodriguez and Jean-Marc Sotiropoulos and Wesley Moran",

year = "2022",

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doi = "10.24820/ark.5550190.p011.745",

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T1 - Computational study on the iodobenzene-catalyzed oxidative cyclization of a δ-alkynyl β-ketoester

AU - Butt, Smaher

AU - Rodriguez, Arantxa

AU - Sotiropoulos, Jean-Marc

AU - Moran, Wesley

PY - 2022/6/12

Y1 - 2022/6/12

N2 - 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.

AB - 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.

KW - DFT calculations

KW - Iodine compounds

KW - Catalysis

KW - Organic Chemistry

KW - Hypervalent iodine

KW - DFT

KW - Alkyne

KW - cyclization

U2 - 10.24820/ark.5550190.p011.745

DO - 10.24820/ark.5550190.p011.745

M3 - Article

VL - 2022

SP - 19

EP - 26

JO - Arkivoc

JF - Arkivoc

SN - 1551-7004

IS - vii

ER -

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

Abstract

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