Meso-Tetraphenylporphyrin Iron Chloride Catalyzed Selective Oxidative Cross-Coupling of Phenols

Hadas Shalit; Anna Libman; Doron Pappo

doi:10.1021/jacs.7b05898

Meso-Tetraphenylporphyrin Iron Chloride Catalyzed Selective Oxidative Cross-Coupling of Phenols

Hadas Shalit, Anna Libman, Doron Pappo

Department of Chemistry

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

81 Scopus citations

Abstract

A novel catalytic system for oxidative cross-coupling of readily oxidized phenols with poor nucleophilic phenolic partners based on an iron meso-tetraphenylporphyrin chloride (Fe[TPP]Cl) complex in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) was developed. The unique chemoselectivity of this reaction is attributed to the coupling between a liberated phenoxyl radical with an iron-ligated phenolic coupling partner. The conditions are scalable for preparing a long list of unsymmetrical biphenols assembled from a less reactive phenolic unit substituted with alkyl or halide groups.

Original language	English
Pages (from-to)	13404-13413
Number of pages	10
Journal	Journal of the American Chemical Society
Volume	139
Issue number	38
DOIs	https://doi.org/10.1021/jacs.7b05898
State	Published - 27 Sep 2017

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/jacs.7b05898

Cite this

@article{a5a10a69a3b542e1b9fedc8fac2ae68a,

title = "Meso-Tetraphenylporphyrin Iron Chloride Catalyzed Selective Oxidative Cross-Coupling of Phenols",

abstract = "A novel catalytic system for oxidative cross-coupling of readily oxidized phenols with poor nucleophilic phenolic partners based on an iron meso-tetraphenylporphyrin chloride (Fe[TPP]Cl) complex in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) was developed. The unique chemoselectivity of this reaction is attributed to the coupling between a liberated phenoxyl radical with an iron-ligated phenolic coupling partner. The conditions are scalable for preparing a long list of unsymmetrical biphenols assembled from a less reactive phenolic unit substituted with alkyl or halide groups.",

author = "Hadas Shalit and Anna Libman and Doron Pappo",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = sep,

day = "27",

doi = "10.1021/jacs.7b05898",

language = "English",

volume = "139",

pages = "13404--13413",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "38",

}

TY - JOUR

T1 - Meso-Tetraphenylporphyrin Iron Chloride Catalyzed Selective Oxidative Cross-Coupling of Phenols

AU - Shalit, Hadas

AU - Libman, Anna

AU - Pappo, Doron

PY - 2017/9/27

Y1 - 2017/9/27

N2 - A novel catalytic system for oxidative cross-coupling of readily oxidized phenols with poor nucleophilic phenolic partners based on an iron meso-tetraphenylporphyrin chloride (Fe[TPP]Cl) complex in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) was developed. The unique chemoselectivity of this reaction is attributed to the coupling between a liberated phenoxyl radical with an iron-ligated phenolic coupling partner. The conditions are scalable for preparing a long list of unsymmetrical biphenols assembled from a less reactive phenolic unit substituted with alkyl or halide groups.

AB - A novel catalytic system for oxidative cross-coupling of readily oxidized phenols with poor nucleophilic phenolic partners based on an iron meso-tetraphenylporphyrin chloride (Fe[TPP]Cl) complex in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) was developed. The unique chemoselectivity of this reaction is attributed to the coupling between a liberated phenoxyl radical with an iron-ligated phenolic coupling partner. The conditions are scalable for preparing a long list of unsymmetrical biphenols assembled from a less reactive phenolic unit substituted with alkyl or halide groups.

UR - http://www.scopus.com/inward/record.url?scp=85030107673&partnerID=8YFLogxK

U2 - 10.1021/jacs.7b05898

DO - 10.1021/jacs.7b05898

M3 - Article

AN - SCOPUS:85030107673

SN - 0002-7863

VL - 139

SP - 13404

EP - 13413

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 38

ER -

Meso-Tetraphenylporphyrin Iron Chloride Catalyzed Selective Oxidative Cross-Coupling of Phenols

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this