Synthetic and Predictive Approach to Unsymmetrical Biphenols by Iron-Catalyzed Chelated Radical-Anion Oxidative Coupling

Anna Libman; Hadas Shalit; Yulia Vainer; Sachin Narute; Sebastian Kozuch; Doron Pappo

doi:10.1021/jacs.5b06494

Synthetic and Predictive Approach to Unsymmetrical Biphenols by Iron-Catalyzed Chelated Radical-Anion Oxidative Coupling

Anna Libman
, Hadas Shalit
, Yulia Vainer
, Sachin Narute
, Sebastian Kozuch
, Doron Pappo

Department of Chemistry

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

153 Scopus citations

Abstract

An iron-catalyzed oxidative unsymmetrical biphenol coupling in 1,1,1,3,3,3-hexafluoropropan-2-ol that proceeds via a chelated radical-anion coupling mechanism was developed. Based on mechanistic studies, electrochemical methods, and density functional theory calculations, we suggest a general model that enables prediction of the feasibility of cross-coupling for a given pair of phenols.

Original language	English
Pages (from-to)	11453-11460
Number of pages	8
Journal	Journal of the American Chemical Society
Volume	137
Issue number	35
DOIs	https://doi.org/10.1021/jacs.5b06494
State	Published - 9 Sep 2015

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.5b06494

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abstract = "An iron-catalyzed oxidative unsymmetrical biphenol coupling in 1,1,1,3,3,3-hexafluoropropan-2-ol that proceeds via a chelated radical-anion coupling mechanism was developed. Based on mechanistic studies, electrochemical methods, and density functional theory calculations, we suggest a general model that enables prediction of the feasibility of cross-coupling for a given pair of phenols.",

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AU - Shalit, Hadas

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AU - Narute, Sachin

AU - Kozuch, Sebastian

AU - Pappo, Doron

PY - 2015/9/9

Y1 - 2015/9/9

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AB - An iron-catalyzed oxidative unsymmetrical biphenol coupling in 1,1,1,3,3,3-hexafluoropropan-2-ol that proceeds via a chelated radical-anion coupling mechanism was developed. Based on mechanistic studies, electrochemical methods, and density functional theory calculations, we suggest a general model that enables prediction of the feasibility of cross-coupling for a given pair of phenols.

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M3 - Article

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JF - Journal of the American Chemical Society

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Synthetic and Predictive Approach to Unsymmetrical Biphenols by Iron-Catalyzed Chelated Radical-Anion Oxidative Coupling

Abstract

ASJC Scopus subject areas

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